| 1999-04-05 | vs NYN | 1 | W 6-2 | 1-0 | 1 | 38,983 | Alex Fernandez | Al Leiter | Alex Fernandez | Al Leiter | | 6 | 2 | 4 |
| 1999-04-06 | vs NYN | 2 | L 3-12 | 2-0 | 1 | 18,075 | Livan Hernandez | Rick Reed | Rick Reed | Livan Hernandez | Allen Watson | 9 | 14 | -5 |
| 1999-04-07 | vs NYN | 3 | L 0-6 | 2-1 | 1 | 13,845 | Jesus Sanchez | Bobby Jones | Bobby Jones | Jesus Sanchez | | 9 | 20 | -11 |
| 1999-04-09 | vs PHI | 4 | W 7-4 | 3-1 | 2 | 13,229 | Brian Meadows | Paul Spoljaric | Brian Meadows | Paul Spoljaric | | 16 | 24 | -8 |
| 1999-04-10 | vs PHI | 5 | L 2-5 | 3-2 | 3 | 22,776 | Dennis Springer | Curt Schilling | Curt Schilling | Dennis Springer | Jeff Brantley | 18 | 29 | -11 |
| 1999-04-11 | vs PHI | 6 | L 1-2 | 3-3 | 3 | 14,954 | Alex Fernandez | Chad Ogea | Chad Ogea | Alex Fernandez | Jeff Brantley | 19 | 31 | -12 |
| 1999-04-12 | @ NYN | 7 | L 1-8 | 3-4 | 5 | 52,052 | Livan Hernandez | Bobby Jones | Bobby Jones | Livan Hernandez | | 20 | 39 | -19 |
| 1999-04-14 | @ NYN | 8 | L 1-4 | 3-5 | 5 | 15,729 | Jesus Sanchez | Orel Hershiser | Orel Hershiser | Jesus Sanchez | John Franco | 21 | 43 | -22 |
| 1999-04-15 | @ NYN | 9 | W 11-4 | 3-6 | 5 | 14,165 | Brian Meadows | Masato Yoshii | Brian Meadows | Masato Yoshii | | 32 | 47 | -15 |
| 1999-04-16 | @ PHI | 10 | L 3-17 | 4-6 | 5 | 12,079 | Dennis Springer | Curt Schilling | Curt Schilling | Dennis Springer | | 35 | 64 | -29 |
| 1999-04-17 | @ PHI | 11 | L 1-2 | 4-7 | 5 | 14,817 | Livan Hernandez | Chad Ogea | Wayne Gomes | Antonio Alfonseca | | 36 | 66 | -30 |
| 1999-04-18 | @ PHI | 12 | L 2-7 | 4-8 | 5 | 17,176 | Kirt Ojala | Carlton Loewer | Carlton Loewer | Kirt Ojala | | 38 | 73 | -35 |
| 1999-04-19 | @ SFN | 13 | L 4-5 | 4-9 | 5 | 10,474 | Jesus Sanchez | Shawn Estes | John Johnstone | Antonio Alfonseca | Robb Nen | 42 | 78 | -36 |
| 1999-04-20 | @ SFN | 14 | W 7-2 | 5-9 | 4 | 10,765 | Brian Meadows | Chris Brock | Brian Meadows | Chris Brock | Brian Edmondson | 49 | 80 | -31 |
| 1999-04-21 | @ SFN | 15 | L 0-4 | 5-10 | 4 | 10,249 | Dennis Springer | Joe Nathan | Joe Nathan | Dennis Springer | | 49 | 84 | -35 |
| 1999-04-23 | vs ATL | 16 | W 9-1 | 6-10 | 4 | 21,713 | Livan Hernandez | Tom Glavine | Livan Hernandez | Tom Glavine | | 58 | 85 | -27 |
| 1999-04-24 | vs ATL | 17 | L 7-8 | 6-11 | 4 | 32,591 | Jesus Sanchez | Greg Maddux | Greg Maddux | Brian Edmondson | John Rocker | 65 | 93 | -28 |
| 1999-04-25 | vs ATL | 18 | L 1-5 | 6-12 | 5 | 28,636 | Brian Meadows | John Smoltz | John Smoltz | Brian Meadows | | 66 | 98 | -32 |
| 1999-04-26 | vs ATL | 19 | L 3-5 | 6-13 | 5 | 15,397 | Dennis Springer | Kevin Millwood | Rudy Seanez | Antonio Alfonseca | | 69 | 103 | -34 |
| 1999-04-27 | vs CHN | 20 | W 8-0 | 7-13 | 5 | 14,596 | Alex Fernandez | Scott Sanders | Brian Edmondson | Scott Sanders | | 77 | 103 | -26 |
| 1999-04-28 | vs CHN | 21 | L 1-6 | 7-14 | 5 | 14,312 | Livan Hernandez | Steve Trachsel | Steve Trachsel | Livan Hernandez | | 78 | 109 | -31 |
| 1999-04-29 | vs CHN | 22 | L 2-5 | 7-15 | 5 | 12,484 | Jesus Sanchez | Kyle Farnsworth | Kyle Farnsworth | Jesus Sanchez | Rod Beck | 80 | 114 | -34 |
| 1999-04-30 | vs HOU | 23 | L 1-8 | 7-16 | 5 | 19,116 | Brian Meadows | Sean Bergman | Sean Bergman | Brian Meadows | | 81 | 122 | -41 |
| 1999-05-01 | vs HOU | 24 | L 4-6 | 7-17 | 5 | 17,604 | Dennis Springer | Jose Lima | Jose Lima | Dennis Springer | Billy Wagner | 85 | 128 | -43 |
| 1999-05-02 | vs HOU | 25 | L 2-3 | 7-18 | 5 | 16,575 | Alex Fernandez | Shane Reynolds | Shane Reynolds | Alex Fernandez | Billy Wagner | 87 | 131 | -44 |
| 1999-05-03 | vs MIL | 26 | L 4-6 | 7-19 | 5 | 8,628 | Livan Hernandez | Steve Woodard | Bob Wickman | Archie Corbin | | 91 | 137 | -46 |
| 1999-05-04 | vs MIL | 27 | L 1-8 | 7-20 | 5 | 10,308 | Jesus Sanchez | Cal Eldred | Cal Eldred | Jesus Sanchez | | 92 | 145 | -53 |
| 1999-05-05 | vs MIL | 28 | L 0-2 | 7-21 | 5 | 13,511 | Brian Meadows | Scott Karl | Scott Karl | Brian Meadows | Bob Wickman | 92 | 147 | -55 |
| 1999-05-07 | @ LAN | 29 | W 6-3 | 8-21 | 5 | 54,009 | Dennis Springer | Darren Dreifort | Dennis Springer | Darren Dreifort | Matt Mantei | 98 | 150 | -52 |
| 1999-05-08 | @ LAN | 30 | L 1-8 | 8-22 | 5 | 36,595 | Livan Hernandez | Kevin Brown | Kevin Brown | Livan Hernandez | | 99 | 158 | -59 |
| 1999-05-09 | @ LAN | 31 | W 6-4 | 9-22 | 5 | 29,397 | Jesus Sanchez | Chan Ho Park | Brian Edmondson | Pedro Borbon | Matt Mantei | 105 | 162 | -57 |
| 1999-05-10 | @ SDN | 32 | L 5-7 | 9-23 | 5 | 12,713 | Brian Meadows | Woody Williams | Dan Miceli | Antonio Alfonseca | Trevor Hoffman | 110 | 169 | -59 |
| 1999-05-11 | @ SDN | 33 | W 5-4 | 10-23 | 5 | 14,188 | Ryan Dempster | Stan Spencer | Ryan Dempster | Stan Spencer | Matt Mantei | 115 | 173 | -58 |
| 1999-05-12 | @ SDN | 34 | L 7-8 | 10-24 | 5 | 14,288 | Dennis Springer | Matt Clement | Donne Wall | Brian Edmondson | Trevor Hoffman | 122 | 181 | -59 |
| 1999-05-14 | @ MIL | 35 | W 14-6 | 10-25 | 5 | 14,923 | Jesus Sanchez | Rafael Roque | Jesus Sanchez | Rafael Roque | Matt Mantei | 136 | 187 | -51 |
| 1999-05-15 | @ MIL | 36 | L 2-7 | 10-26 | 5 | 15,695 | Brian Meadows | Steve Woodard | Steve Woodard | Brian Meadows | | 138 | 194 | -56 |
| 1999-05-16 | @ MIL | 37 | W 3-2 | 11-26 | 5 | 16,353 | Livan Hernandez | Hideo Nomo | Livan Hernandez | Hideo Nomo | Matt Mantei | 141 | 196 | -55 |
| 1999-05-17 | vs CHN | 38 | L 1-8 | 11-27 | 5 | 13,113 | Ryan Dempster | Kevin Tapani | Kevin Tapani | Ryan Dempster | | 142 | 204 | -62 |
| 1999-05-18 | vs CHN | 39 | L 1-4 | 11-28 | 5 | 13,504 | Alex Fernandez | Terry Mulholland | Felix Heredia | Dennis Springer | Scott Sanders | 143 | 208 | -65 |
| 1999-05-19 | vs CHN | 40 | L 7-8 | 11-29 | 5 | 15,059 | Jesus Sanchez | Jon Lieber | Rodney Myers | Matt Mantei | Terry Adams | 150 | 216 | -66 |
| 1999-05-20 | vs PIT | 41 | W 4-3 | 12-29 | 6 | 11,473 | Brian Meadows | Kris Benson | Antonio Alfonseca | Mike Williams | | 154 | 219 | -65 |
| 1999-05-21 | vs PIT | 42 | W 8-1 | 13-29 | 5 | 16,782 | Livan Hernandez | Pete Schourek | Livan Hernandez | Pete Schourek | | 162 | 220 | -58 |
| 1999-05-22 | vs PIT | 43 | L 4-11 | 14-29 | 5 | 23,121 | Ryan Dempster | Todd Ritchie | Todd Ritchie | Dennis Springer | | 166 | 231 | -65 |
| 1999-05-23 | vs PIT | 44 | L 5-6 | 14-30 | 5 | 19,321 | Alex Fernandez | Jason Schmidt | Jeff Wallace | Vic Darensbourg | Mike Williams | 171 | 237 | -66 |
| 1999-05-24 | @ CHN | 45 | W 7-5 | 15-30 | 5 | 31,987 | Jesus Sanchez | Jon Lieber | Matt Mantei | Rick Aguilera | | 178 | 242 | -64 |
| 1999-05-25 | @ CHN | 46 | W 6-3 | 16-30 | 5 | 35,141 | Brian Meadows | Steve Trachsel | Brian Meadows | Steve Trachsel | | 184 | 245 | -61 |
| 1999-05-26 | @ CHN | 47 | L 4-6 | 16-31 | 5 | 38,708 | Livan Hernandez | Kyle Farnsworth | Rick Aguilera | Braden Looper | | 188 | 251 | -63 |
| 1999-05-28 | vs CIN | 48 | W 8-1 | 17-31 | 5 | 14,975 | Ryan Dempster | Steve Avery | Ryan Dempster | Steve Avery | | 196 | 252 | -56 |
| 1999-05-29 | vs CIN | 49 | L 1-8 | 17-32 | 5 | 16,870 | Alex Fernandez | Jason Bere | Jason Bere | Alex Fernandez | | 197 | 260 | -63 |
| 1999-05-30 | vs CIN | 50 | L 4-6 | 17-33 | 5 | 13,851 | Dennis Springer | Steve Parris | Danny Graves | Brian Edmondson | | 201 | 266 | -65 |
| 1999-05-31 | vs SLN | 51 | L 2-5 | 17-34 | 5 | 21,943 | Brian Meadows | Kent Bottenfield | Kent Bottenfield | Brian Meadows | Ricky Bottalico | 203 | 271 | -68 |
| 1999-06-01 | vs SLN | 52 | L 4-8 | 17-35 | 5 | 18,747 | Livan Hernandez | Juan Acevedo | Juan Acevedo | Livan Hernandez | | 207 | 279 | -72 |
| 1999-06-02 | vs SLN | 53 | W 10-2 | 17-36 | 5 | 16,733 | Ryan Dempster | Lance Painter | Ryan Dempster | Lance Painter | | 217 | 281 | -64 |
| 1999-06-03 | vs SLN | 54 | W 4-2 | 18-36 | 5 | 15,751 | Alex Fernandez | Darren Oliver | Braden Looper | Darren Oliver | Matt Mantei | 221 | 283 | -62 |
| 1999-06-04 | @ TBA | 55 | W 10-0 | 19-36 | 5 | 20,167 | Dennis Springer | Ryan Rupe | Dennis Springer | Ryan Rupe | | 231 | 283 | -52 |
| 1999-06-05 | @ TBA | 56 | W 9-7 | 20-36 | 5 | 22,686 | Brian Meadows | Bryan Rekar | Brian Meadows | Mike Duvall | Matt Mantei | 240 | 290 | -50 |
| 1999-06-06 | @ TBA | 57 | W 11-6 | 20-37 | 5 | 21,321 | Livan Hernandez | Bobby Witt | Antonio Alfonseca | Esteban Yan | | 251 | 296 | -45 |
| 1999-06-08 | vs BAL | 58 | W 2-1 | 21-37 | 6 | 0 | Ryan Dempster | Mike Mussina | Brian Edmondson | Mike Timlin | | 253 | 297 | -44 |
| 1999-06-08 | vs BAL | 59 | W 5-3 | 21-37 | 6 | 13,003 | Alex Fernandez | Jason Johnson | Antonio Alfonseca | Scott Kamieniecki | Matt Mantei | 258 | 300 | -42 |
| 1999-06-09 | vs BAL | 60 | L 2-4 | 22-38 | 5 | 12,851 | Dennis Springer | Scott Erickson | Scott Erickson | Dennis Springer | Arthur Rhodes | 260 | 304 | -44 |
| 1999-06-11 | vs NYA | 61 | L 4-8 | 22-39 | 5 | 40,161 | Brian Meadows | Orlando Hernandez | Orlando Hernandez | Brian Meadows | Mariano Rivera | 264 | 312 | -48 |
| 1999-06-12 | vs NYA | 62 | L 4-5 | 22-40 | 5 | 42,110 | Livan Hernandez | Roger Clemens | Roger Clemens | Livan Hernandez | Mariano Rivera | 268 | 317 | -49 |
| 1999-06-13 | vs NYA | 63 | W 8-2 | 23-40 | 5 | 39,639 | Alex Fernandez | Andy Pettitte | Alex Fernandez | Andy Pettitte | | 276 | 319 | -43 |
| 1999-06-14 | @ ARI | 64 | L 0-2 | 23-41 | 5 | 39,314 | Ryan Dempster | Randy Johnson | Randy Johnson | Ryan Dempster | Gregg Olson | 276 | 321 | -45 |
| 1999-06-15 | @ ARI | 65 | L 3-4 | 23-42 | 5 | 30,096 | Dennis Springer | Brian Anderson | Brian Anderson | Dennis Springer | Gregg Olson | 279 | 325 | -46 |
| 1999-06-16 | @ ARI | 66 | L 6-12 | 24-42 | 5 | 30,567 | Brian Meadows | Armando Reynoso | Armando Reynoso | Brian Meadows | | 285 | 337 | -52 |
| 1999-06-18 | @ COL | 67 | L 10-11 | 24-43 | 5 | 46,394 | Livan Hernandez | Pedro Astacio | Chuck McElroy | Matt Mantei | | 295 | 348 | -53 |
| 1999-06-19 | @ COL | 68 | L 2-10 | 25-43 | 5 | 47,051 | Alex Fernandez | Bobby Jones | Bobby Jones | Alex Fernandez | | 297 | 358 | -61 |
| 1999-06-20 | @ COL | 69 | L 7-8 | 25-44 | 5 | 47,070 | Ryan Dempster | Brian Bohanon | Brian Bohanon | Ryan Dempster | Dave Veres | 304 | 366 | -62 |
| 1999-06-22 | @ NYN | 70 | L 2-8 | 25-45 | 5 | 30,713 | Dennis Springer | Masato Yoshii | Greg McMichael | Dennis Springer | Armando Benitez | 306 | 374 | -68 |
| 1999-06-23 | @ NYN | 71 | L 3-6 | 25-46 | 5 | 25,116 | Brian Meadows | Al Leiter | Al Leiter | Brian Meadows | John Franco | 309 | 380 | -71 |
| 1999-06-24 | @ NYN | 72 | L 2-3 | 25-47 | 5 | 29,567 | Livan Hernandez | Orel Hershiser | Dennis Cook | Livan Hernandez | John Franco | 311 | 383 | -72 |
| 1999-06-25 | @ MON | 73 | L 3-4 | 25-48 | 5 | 6,630 | Alex Fernandez | Carl Pavano | Carl Pavano | Alex Fernandez | Ugueth Urbina | 314 | 387 | -73 |
| 1999-06-26 | @ MON | 74 | W 9-3 | 26-48 | 5 | 6,540 | Ryan Dempster | Dan Smith | Ryan Dempster | Dan Smith | | 323 | 390 | -67 |
| 1999-06-27 | @ MON | 75 | W 4-3 | 27-48 | 5 | 10,208 | Dennis Springer | Mike Thurman | Dennis Springer | Mike Thurman | Matt Mantei | 327 | 393 | -66 |
| 1999-06-28 | vs NYN | 76 | L 4-10 | 28-48 | 5 | 12,444 | Brian Meadows | Al Leiter | Al Leiter | Brian Meadows | | 331 | 403 | -72 |
| 1999-06-29 | vs NYN | 77 | L 1-5 | 28-49 | 5 | 11,256 | Livan Hernandez | Orel Hershiser | Orel Hershiser | Livan Hernandez | | 332 | 408 | -76 |
| 1999-06-30 | vs NYN | 78 | W 4-3 | 29-49 | 5 | 16,660 | Alex Fernandez | Rick Reed | Antonio Alfonseca | Armando Benitez | | 336 | 411 | -75 |
| 1999-07-01 | vs NYN | 79 | L 8-12 | 30-49 | 5 | 10,884 | Ryan Dempster | Octavio Dotel | Octavio Dotel | Ryan Dempster | | 344 | 423 | -79 |
| 1999-07-03 | vs MON | 80 | W 6-1 | 31-49 | 5 | 24,186 | Brian Meadows | Mike Thurman | Brian Meadows | Miguel Batista | | 350 | 424 | -74 |
| 1999-07-04 | vs MON | 81 | W 5-1 | 32-49 | 5 | 16,971 | Livan Hernandez | Jeremy Powell | Livan Hernandez | Jeremy Powell | | 355 | 425 | -70 |
| 1999-07-05 | @ ATL | 82 | L 5-6 | 32-50 | 5 | 37,506 | Dennis Springer | Odalis Perez | Kevin McGlinchy | Antonio Alfonseca | | 360 | 431 | -71 |
| 1999-07-06 | @ ATL | 83 | W 5-2 | 33-50 | 5 | 32,665 | Alex Fernandez | Tom Glavine | Alex Fernandez | Tom Glavine | Matt Mantei | 365 | 433 | -68 |
| 1999-07-07 | @ ATL | 84 | L 3-7 | 33-51 | 5 | 35,610 | Ryan Dempster | Greg Maddux | Greg Maddux | Ryan Dempster | | 368 | 440 | -72 |
| 1999-07-08 | @ ATL | 85 | L 2-5 | 33-52 | 5 | 36,606 | Brian Meadows | Kevin Millwood | Kevin Millwood | Brian Meadows | | 370 | 445 | -75 |
| 1999-07-09 | vs TBA | 86 | W 11-4 | 33-53 | 5 | 17,976 | Livan Hernandez | Ryan Rupe | Livan Hernandez | Ryan Rupe | | 381 | 449 | -68 |
| 1999-07-10 | vs TBA | 87 | L 8-9 | 33-54 | 5 | 26,516 | Dennis Springer | Bryan Rekar | Bryan Rekar | Dennis Springer | Roberto Hernandez | 389 | 458 | -69 |
| 1999-07-11 | vs TBA | 88 | W 3-2 | 34-54 | 5 | 19,984 | Alex Fernandez | Wilson Alvarez | Alex Fernandez | Wilson Alvarez | Antonio Alfonseca | 392 | 460 | -68 |
| 1999-07-15 | @ TOR | 89 | W 8-6 | 35-54 | 5 | 25,072 | Livan Hernandez | Chris Carpenter | Braden Looper | Billy Koch | Antonio Alfonseca | 400 | 466 | -66 |
| 1999-07-16 | @ TOR | 90 | W 4-2 | 36-54 | 5 | 22,449 | Dennis Springer | Pat Hentgen | Dennis Springer | Pat Hentgen | Antonio Alfonseca | 404 | 468 | -64 |
| 1999-07-17 | @ TOR | 91 | L 1-6 | 36-55 | 5 | 27,159 | Alex Fernandez | David Wells | David Wells | Brian Edmondson | | 405 | 474 | -69 |
| 1999-07-18 | @ BOS | 92 | L 9-11 | 37-55 | 5 | 30,288 | Ryan Dempster | Pedro Martinez | Derek Lowe | Vladimir Nunez | Tim Wakefield | 414 | 485 | -71 |
| 1999-07-19 | @ BOS | 93 | W 10-7 | 37-56 | 5 | 23,282 | Brian Meadows | Tomo Ohka | Brian Meadows | Tomo Ohka | Antonio Alfonseca | 424 | 492 | -68 |
| 1999-07-20 | @ BOS | 94 | L 1-7 | 37-57 | 5 | 25,346 | Livan Hernandez | Brian Rose | Brian Rose | Livan Hernandez | | 425 | 499 | -74 |
| 1999-07-21 | vs ATL | 95 | W 2-0 | 38-57 | 5 | 15,509 | Dennis Springer | Greg Maddux | Dennis Springer | Greg Maddux | | 427 | 499 | -72 |
| 1999-07-22 | vs ATL | 96 | L 3-6 | 38-58 | 5 | 17,759 | Alex Fernandez | Odalis Perez | Kevin McGlinchy | Alex Fernandez | John Rocker | 430 | 505 | -75 |
| 1999-07-23 | vs MIL | 97 | W 5-4 | 39-58 | 7 | 19,745 | Ryan Dempster | Bill Pulsipher | Vladimir Nunez | Bob Wickman | | 435 | 509 | -74 |
| 1999-07-24 | vs MIL | 98 | W 4-1 | 40-58 | 5 | 21,033 | Brian Meadows | Kyle Peterson | Brian Meadows | Kyle Peterson | Antonio Alfonseca | 439 | 510 | -71 |
| 1999-07-25 | vs MIL | 99 | W 4-3 | 41-58 | 4 | 14,862 | Dennis Springer | Steve Woodard | Jesus Sanchez | David Weathers | Antonio Alfonseca | 443 | 513 | -70 |
| 1999-07-26 | @ PHI | 100 | L 1-9 | 41-59 | 5 | 16,047 | Vladimir Nunez | Robert Person | Robert Person | Vladimir Nunez | | 444 | 522 | -78 |
| 1999-07-27 | @ PHI | 101 | W 6-2 | 42-59 | 4 | 18,282 | Alex Fernandez | Randy Wolf | Alex Fernandez | Randy Wolf | Antonio Alfonseca | 450 | 524 | -74 |
| 1999-07-28 | @ PHI | 102 | L 4-9 | 42-60 | 5 | 17,497 | Ryan Dempster | Steve Schrenk | Steve Schrenk | Ryan Dempster | | 454 | 533 | -79 |
| 1999-07-29 | @ PHI | 103 | L 1-12 | 42-61 | 5 | 26,834 | Brian Meadows | Chad Ogea | Chad Ogea | Brian Meadows | | 455 | 545 | -90 |
| 1999-07-30 | @ PIT | 104 | W 8-7 | 43-61 | 5 | 25,163 | Dennis Springer | Pete Schourek | Brian Edmondson | Greg Hansell | Antonio Alfonseca | 463 | 552 | -89 |
| 1999-07-31 | @ PIT | 105 | L 2-4 | 43-62 | 5 | 33,862 | Vladimir Nunez | Jason Schmidt | Jason Schmidt | Brian Edmondson | Mike Williams | 465 | 556 | -91 |
| 1999-08-01 | @ PIT | 106 | L 1-2 | 43-63 | 5 | 19,071 | Alex Fernandez | Francisco Cordova | Francisco Cordova | Alex Fernandez | | 466 | 558 | -92 |
| 1999-08-03 | vs PHI | 107 | L 5-6 | 43-64 | 5 | 10,223 | Ryan Dempster | Chad Ogea | Amaury Telemaco | Brian Edmondson | Wayne Gomes | 471 | 564 | -93 |
| 1999-08-04 | vs PHI | 108 | L 1-4 | 43-65 | 5 | 10,445 | Dennis Springer | Paul Byrd | Paul Byrd | Dennis Springer | Steve Schrenk | 472 | 568 | -96 |
| 1999-08-05 | vs PHI | 109 | L 3-9 | 43-66 | 5 | 9,610 | Vladimir Nunez | Robert Person | Robert Person | Vladimir Nunez | | 475 | 577 | -102 |
| 1999-08-06 | vs COL | 110 | W 9-1 | 44-66 | 5 | 14,032 | Alex Fernandez | Bobby Jones | Alex Fernandez | Bobby Jones | | 484 | 578 | -94 |
| 1999-08-07 | vs COL | 111 | W 4-1 | 45-66 | 5 | 18,469 | Brian Meadows | Brian Bohanon | Brian Meadows | Brian Bohanon | Antonio Alfonseca | 488 | 579 | -91 |
| 1999-08-08 | vs COL | 112 | W 2-1 | 46-66 | 5 | 17,691 | Ryan Dempster | Jamey Wright | Ryan Dempster | Jamey Wright | Antonio Alfonseca | 490 | 580 | -90 |
| 1999-08-09 | vs SFN | 113 | W 5-4 | 47-66 | 5 | 10,768 | Dennis Springer | Livan Hernandez | Jesus Sanchez | John Johnstone | | 495 | 584 | -89 |
| 1999-08-10 | vs SFN | 114 | W 8-7 | 48-66 | 5 | 13,553 | Vladimir Nunez | Mark Gardner | Brian Edmondson | Felix Rodriguez | | 503 | 591 | -88 |
| 1999-08-11 | vs SFN | 115 | W 6-5 | 49-66 | 5 | 16,709 | Alex Fernandez | Shawn Estes | Jesus Sanchez | Robb Nen | | 509 | 596 | -87 |
| 1999-08-13 | @ SDN | 116 | W 4-3 | 50-66 | 6 | 48,743 | Brian Meadows | Brian Boehringer | Brian Meadows | Brian Boehringer | Antonio Alfonseca | 513 | 599 | -86 |
| 1999-08-14 | @ SDN | 117 | L 4-6 | 50-67 | 5 | 61,355 | Ryan Dempster | Matt Clement | Matt Clement | Jesus Sanchez | Trevor Hoffman | 517 | 605 | -88 |
| 1999-08-15 | @ SDN | 118 | L 6-7 | 50-68 | 6 | 26,325 | Dennis Springer | Andy Ashby | Andy Ashby | Dennis Springer | Trevor Hoffman | 523 | 612 | -89 |
| 1999-08-16 | @ LAN | 119 | W 7-5 | 51-68 | 5 | 26,754 | Vladimir Nunez | Chan Ho Park | Vladimir Nunez | Chan Ho Park | | 530 | 617 | -87 |
| 1999-08-17 | @ LAN | 120 | W 6-1 | 52-68 | 5 | 30,354 | A.J. Burnett | Mike Judd | A.J. Burnett | Mike Judd | Dennis Springer | 536 | 618 | -82 |
| 1999-08-18 | @ LAN | 121 | L 0-7 | 52-69 | 5 | 36,463 | Brian Meadows | Darren Dreifort | Darren Dreifort | Brian Meadows | | 536 | 625 | -89 |
| 1999-08-20 | vs HOU | 122 | L 4-6 | 52-70 | 5 | 19,845 | Ryan Dempster | Shane Reynolds | Trever Miller | Jesus Sanchez | Billy Wagner | 540 | 631 | -91 |
| 1999-08-21 | vs HOU | 123 | L 4-5 | 52-71 | 5 | 25,947 | Dennis Springer | Jose Lima | Doug Henry | Brian Edmondson | Billy Wagner | 544 | 636 | -92 |
| 1999-08-24 | vs ARI | 124 | L 4-5 | 52-72 | 5 | 13,689 | Alex Fernandez | Andy Benes | Andy Benes | Armando Almanza | Matt Mantei | 548 | 641 | -93 |
| 1999-08-25 | vs ARI | 125 | L 2-7 | 52-73 | 5 | 14,409 | Vladimir Nunez | Todd Stottlemyre | Todd Stottlemyre | Vladimir Nunez | | 550 | 648 | -98 |
| 1999-08-26 | vs ARI | 126 | L 2-12 | 53-73 | 5 | 13,521 | Brian Meadows | Randy Johnson | Randy Johnson | Brian Meadows | | 552 | 660 | -108 |
| 1999-08-27 | @ HOU | 127 | L 2-3 | 53-74 | 6 | 0 | Dennis Springer | Jose Lima | Jose Lima | Dennis Springer | Billy Wagner | 554 | 663 | -109 |
| 1999-08-27 | @ HOU | 128 | W 3-1 | 53-74 | 6 | 39,885 | Ryan Dempster | Chris Holt | Ryan Dempster | Chris Holt | Antonio Alfonseca | 557 | 664 | -107 |
| 1999-08-28 | @ HOU | 129 | W 5-2 | 55-74 | 6 | 42,968 | A.J. Burnett | Scott Elarton | A.J. Burnett | Scott Elarton | Antonio Alfonseca | 562 | 666 | -104 |
| 1999-08-29 | @ HOU | 130 | L 4-10 | 56-74 | 5 | 33,666 | Alex Fernandez | Mike Hampton | Mike Hampton | Alex Fernandez | | 566 | 676 | -110 |
| 1999-08-30 | @ SLN | 131 | W 4-2 | 57-74 | 5 | 33,157 | Vladimir Nunez | Kent Bottenfield | Vladimir Nunez | Kent Bottenfield | Antonio Alfonseca | 570 | 678 | -108 |
| 1999-08-31 | @ SLN | 132 | L 1-8 | 57-75 | 5 | 27,476 | Brian Meadows | Larry Luebbers | Larry Luebbers | Brian Meadows | | 571 | 686 | -115 |
| 1999-09-01 | @ SLN | 133 | L 3-9 | 57-76 | 5 | 28,253 | Ryan Dempster | Garrett Stephenson | Garrett Stephenson | Ryan Dempster | | 574 | 695 | -121 |
| 1999-09-03 | vs SDN | 134 | L 3-6 | 57-77 | 5 | 12,581 | A.J. Burnett | Woody Williams | Woody Williams | A.J. Burnett | Trevor Hoffman | 577 | 701 | -124 |
| 1999-09-04 | vs SDN | 135 | W 6-4 | 58-77 | 5 | 25,478 | Alex Fernandez | Buddy Carlyle | Alex Fernandez | Buddy Carlyle | Antonio Alfonseca | 583 | 705 | -122 |
| 1999-09-05 | vs SDN | 136 | L 2-5 | 58-78 | 5 | 15,875 | Vladimir Nunez | Matt Clement | Matt Clement | Vladimir Nunez | Trevor Hoffman | 585 | 710 | -125 |
| 1999-09-06 | vs LAN | 137 | W 8-6 | 59-78 | 5 | 12,089 | Brian Meadows | Ismael Valdez | Brian Meadows | Ismael Valdez | Antonio Alfonseca | 593 | 716 | -123 |
| 1999-09-07 | vs LAN | 138 | W 2-1 | 60-78 | 5 | 13,644 | Ryan Dempster | Eric Gagne | Jesus Sanchez | Matt Herges | Antonio Alfonseca | 595 | 717 | -122 |
| 1999-09-08 | vs LAN | 139 | W 5-4 | 61-78 | 5 | 9,615 | Michael Tejera | Chan Ho Park | Rafael Medina | Onan Masaoka | | 600 | 721 | -121 |
| 1999-09-10 | @ CIN | 140 | L 2-4 | 61-79 | 5 | 23,262 | Dennis Springer | Denny Neagle | Denny Neagle | Dennis Springer | Danny Graves | 602 | 725 | -123 |
| 1999-09-11 | @ CIN | 141 | L 4-12 | 62-79 | 5 | 25,743 | Vladimir Nunez | Juan Guzman | Juan Guzman | Vladimir Nunez | | 606 | 737 | -131 |
| 1999-09-12 | @ CIN | 142 | L 5-11 | 63-79 | 5 | 20,363 | A.J. Burnett | Ron Villone | Ron Villone | A.J. Burnett | | 611 | 748 | -137 |
| 1999-09-13 | @ CIN | 143 | L 4-7 | 63-80 | 5 | 15,298 | Brian Meadows | Steve Parris | Steve Parris | Jesus Sanchez | Danny Graves | 615 | 755 | -140 |
| 1999-09-14 | @ SFN | 144 | L 0-3 | 63-81 | 5 | 16,335 | Ryan Dempster | Shawn Estes | Shawn Estes | Ryan Dempster | | 615 | 758 | -143 |
| 1999-09-15 | @ SFN | 145 | L 3-4 | 63-82 | 5 | 11,996 | Dennis Springer | Russ Ortiz | Russ Ortiz | Dennis Springer | Robb Nen | 618 | 762 | -144 |
| 1999-09-16 | @ SFN | 146 | L 5-6 | 63-83 | 5 | 14,095 | Vladimir Nunez | Kirk Rueter | Bronswell Patrick | Vladimir Nunez | Robb Nen | 623 | 768 | -145 |
| 1999-09-17 | @ ARI | 147 | W 10-6 | 63-84 | 5 | 34,127 | A.J. Burnett | Andy Benes | A.J. Burnett | Andy Benes | | 633 | 774 | -141 |
| 1999-09-18 | @ ARI | 148 | L 6-8 | 63-85 | 5 | 40,903 | Brian Meadows | Randy Johnson | Greg Swindell | Hector Almonte | | 639 | 782 | -143 |
| 1999-09-19 | @ ARI | 149 | L 7-8 | 63-86 | 5 | 34,752 | Ryan Dempster | Todd Stottlemyre | Gregg Olson | Braden Looper | | 646 | 790 | -144 |
| 1999-09-21 | vs MON | 150 | W 5-3 | 64-86 | 7 | 0 | Dennis Springer | Javier Vazquez | Dennis Springer | Anthony Telford | Antonio Alfonseca | 651 | 793 | -142 |
| 1999-09-21 | vs MON | 151 | W 4-0 | 64-86 | 7 | 8,468 | Reid Cornelius | Jeremy Powell | Reid Cornelius | Jeremy Powell | | 655 | 793 | -138 |
| 1999-09-22 | vs MON | 152 | L 3-5 | 65-87 | 5 | 9,524 | Vladimir Nunez | Miguel Batista | Miguel Batista | Vladimir Nunez | Ugueth Urbina | 658 | 798 | -140 |
| 1999-09-23 | vs MON | 153 | W 2-1 | 66-87 | 5 | 8,886 | A.J. Burnett | Dustin Hermanson | A.J. Burnett | Dustin Hermanson | Antonio Alfonseca | 660 | 799 | -139 |
| 1999-09-24 | vs COL | 154 | L 3-5 | 66-88 | 5 | 18,941 | Brian Meadows | Pedro Astacio | Pedro Astacio | Brian Edmondson | Dave Veres | 663 | 804 | -141 |
| 1999-09-25 | vs COL | 155 | W 8-2 | 67-88 | 5 | 27,271 | Ryan Dempster | John Thomson | Ryan Dempster | John Thomson | | 671 | 806 | -135 |
| 1999-09-26 | vs COL | 156 | L 6-8 | 67-89 | 5 | 26,012 | Dennis Springer | Jamey Wright | Curt Leskanic | Rafael Medina | Dave Veres | 677 | 814 | -137 |
| 1999-09-27 | @ MON | 157 | L 4-8 | 67-90 | 5 | 5,156 | Reid Cornelius | Miguel Batista | Anthony Telford | Hector Almonte | | 681 | 822 | -141 |
| 1999-09-28 | @ MON | 158 | W 5-3 | 68-90 | 5 | 5,785 | Vladimir Nunez | Dustin Hermanson | Vladimir Nunez | Dustin Hermanson | Antonio Alfonseca | 686 | 825 | -139 |
| 1999-09-29 | @ MON | 159 | L 3-5 | 68-91 | 5 | 11,689 | A.J. Burnett | Ted Lilly | Steve Kline | Braden Looper | Ugueth Urbina | 689 | 830 | -141 |
| 1999-10-01 | @ ATL | 160 | L 1-4 | 68-92 | 5 | 38,413 | Brian Meadows | John Smoltz | John Smoltz | Brian Meadows | John Rocker | 690 | 834 | -144 |
| 1999-10-02 | @ ATL | 161 | W 1-0 | 69-92 | 5 | 45,394 | Ryan Dempster | Bruce Chen | Braden Looper | Derrin Ebert | Antonio Alfonseca | 691 | 834 | -143 |
| 1999-10-03 | @ ATL | 162 | L 0-18 | 69-93 | 5 | 40,570 | Dennis Springer | Tom Glavine | Tom Glavine | Dennis Springer | | 691 | 852 | -161 |