| 1999-04-05 | vs DET | 1 | L 5-11 | 1-0 | 2 | 46,650 | Rick Helling | Brian Moehler | Brian Moehler | Rick Helling | | 5 | 11 | -6 |
| 1999-04-06 | vs DET | 2 | W 6-0 | 2-0 | 2 | 28,329 | Aaron Sele | Justin Thompson | Aaron Sele | Justin Thompson | | 11 | 11 | 0 |
| 1999-04-07 | vs DET | 3 | W 10-7 | 2-1 | 2 | 25,004 | Mark Clark | Willie Blair | Mike Morgan | Willie Blair | John Wetteland | 21 | 18 | 3 |
| 1999-04-09 | vs ANA | 4 | L 4-8 | 2-2 | 3 | 31,633 | John Burkett | Chuck Finley | Chuck Finley | John Burkett | | 25 | 26 | -1 |
| 1999-04-10 | vs ANA | 5 | L 0-10 | 2-3 | 3 | 37,974 | Rick Helling | Omar Olivares | Omar Olivares | Rick Helling | | 25 | 36 | -11 |
| 1999-04-11 | vs ANA | 6 | W 6-3 | 3-3 | 3 | 23,175 | Aaron Sele | Tim Belcher | Aaron Sele | Tim Belcher | John Wetteland | 31 | 39 | -8 |
| 1999-04-12 | vs ANA | 7 | L 5-13 | 4-3 | 2 | 24,601 | Mark Clark | Ken Hill | Mike Magnante | Mark Clark | | 36 | 52 | -16 |
| 1999-04-13 | @ SEA | 8 | W 15-6 | 4-4 | 2 | 20,710 | Mike Morgan | Ken Cloude | Mike Morgan | Ken Cloude | | 51 | 58 | -7 |
| 1999-04-14 | @ SEA | 9 | W 9-6 | 5-4 | 2 | 20,123 | John Burkett | Butch Henry | Jeff Zimmerman | Jose Paniagua | John Wetteland | 60 | 64 | -4 |
| 1999-04-15 | @ SEA | 10 | W 4-3 | 6-4 | 2 | 22,145 | Rick Helling | Jeff Fassero | Tim Crabtree | John Halama | John Wetteland | 64 | 67 | -3 |
| 1999-04-16 | @ OAK | 11 | L 2-8 | 6-5 | 2 | 9,158 | Aaron Sele | Tom Candiotti | Tom Candiotti | Aaron Sele | | 66 | 75 | -9 |
| 1999-04-17 | @ OAK | 12 | L 3-11 | 7-5 | 2 | 16,271 | Mark Clark | Jimmy Haynes | Jimmy Haynes | Mark Clark | | 69 | 86 | -17 |
| 1999-04-18 | @ OAK | 13 | W 6-2 | 8-5 | 2 | 14,460 | Mike Morgan | Mike Oquist | Mike Morgan | Mike Oquist | | 75 | 88 | -13 |
| 1999-04-20 | @ NYA | 14 | L 0-4 | 8-6 | 2 | 24,514 | John Burkett | David Cone | David Cone | John Burkett | | 75 | 92 | -17 |
| 1999-04-21 | @ NYA | 15 | L 2-4 | 8-7 | 2 | 23,984 | Rick Helling | Roger Clemens | Roger Clemens | Rick Helling | Mariano Rivera | 77 | 96 | -19 |
| 1999-04-22 | @ MIN | 16 | W 6-4 | 9-7 | 1 | 11,221 | Aaron Sele | Eric Milton | Aaron Sele | Eric Milton | John Wetteland | 83 | 100 | -17 |
| 1999-04-23 | @ MIN | 17 | W 4-2 | 10-7 | 1 | 15,321 | Mark Clark | Mike Lincoln | Mark Clark | Mike Lincoln | John Wetteland | 87 | 102 | -15 |
| 1999-04-24 | @ MIN | 18 | W 7-2 | 11-7 | 1 | 19,479 | Mike Morgan | LaTroy Hawkins | Mike Morgan | LaTroy Hawkins | | 94 | 104 | -10 |
| 1999-04-25 | @ MIN | 19 | W 9-5 | 12-7 | 1 | 14,801 | Rick Helling | Dan Perkins | Rick Helling | Dan Perkins | | 103 | 109 | -6 |
| 1999-04-27 | vs NYA | 20 | L 6-7 | 12-8 | 1 | 42,690 | Aaron Sele | Roger Clemens | Mike Stanton | John Wetteland | Mariano Rivera | 109 | 116 | -7 |
| 1999-04-28 | vs NYA | 21 | W 8-6 | 13-8 | 1 | 33,038 | Mark Clark | Orlando Hernandez | Mike Munoz | Mike Stanton | John Wetteland | 117 | 122 | -5 |
| 1999-04-29 | vs NYA | 22 | L 3-5 | 13-9 | 1 | 35,573 | Mike Morgan | Ramiro Mendoza | Ramiro Mendoza | Mike Morgan | Mariano Rivera | 120 | 127 | -7 |
| 1999-04-30 | vs CLE | 23 | W 7-5 | 14-9 | 1 | 36,556 | Rick Helling | Bartolo Colon | Rick Helling | Bartolo Colon | John Wetteland | 127 | 132 | -5 |
| 1999-05-01 | vs CLE | 24 | L 3-5 | 14-10 | 1 | 45,579 | Aaron Sele | Dwight Gooden | Dwight Gooden | Aaron Sele | Michael Jackson | 130 | 137 | -7 |
| 1999-05-02 | vs CLE | 25 | W 8-6 | 15-10 | 1 | 29,921 | Mark Clark | Charles Nagy | Mark Clark | Charles Nagy | John Wetteland | 138 | 143 | -5 |
| 1999-05-03 | vs CLE | 26 | L 4-10 | 16-10 | 1 | 31,181 | Mike Morgan | Jaret Wright | Jaret Wright | Mike Morgan | | 142 | 153 | -11 |
| 1999-05-05 | @ BOS | 27 | W 8-3 | 17-10 | 1 | 20,960 | Rick Helling | Pat Rapp | Rick Helling | Pat Rapp | | 150 | 156 | -6 |
| 1999-05-06 | @ BOS | 28 | L 2-3 | 17-11 | 1 | 21,412 | Aaron Sele | Bret Saberhagen | Rheal Cormier | Aaron Sele | Tim Wakefield | 152 | 159 | -7 |
| 1999-05-07 | @ TOR | 29 | L 6-9 | 17-12 | 1 | 22,110 | Mark Clark | Pat Hentgen | Pat Hentgen | Mark Clark | Billy Koch | 158 | 168 | -10 |
| 1999-05-08 | @ TOR | 30 | W 4-3 | 18-12 | 1 | 24,642 | Mike Morgan | David Wells | Mike Morgan | David Wells | John Wetteland | 162 | 171 | -9 |
| 1999-05-09 | @ TOR | 31 | W 11-6 | 18-13 | 1 | 20,374 | John Burkett | Roy Halladay | Danny Patterson | Peter Munro | | 173 | 177 | -4 |
| 1999-05-10 | @ CHA | 32 | L 2-5 | 18-14 | 1 | 12,670 | Rick Helling | Jaime Navarro | Jaime Navarro | Rick Helling | | 175 | 182 | -7 |
| 1999-05-11 | @ CHA | 33 | W 11-5 | 18-15 | 1 | 10,905 | Esteban Loaiza | James Baldwin | Jeff Zimmerman | Bob Howry | | 186 | 187 | -1 |
| 1999-05-13 | vs BAL | 34 | W 15-7 | 18-16 | 1 | 40,678 | Mike Morgan | Scott Kamieniecki | Mike Morgan | Scott Kamieniecki | | 201 | 194 | 7 |
| 1999-05-14 | vs BAL | 35 | W 7-6 | 19-16 | 1 | 36,665 | Mark Clark | Scott Erickson | Tim Crabtree | Arthur Rhodes | John Wetteland | 208 | 200 | 8 |
| 1999-05-15 | vs BAL | 36 | W 8-1 | 20-16 | 1 | 46,118 | Rick Helling | Juan Guzman | Rick Helling | Doug Johns | | 216 | 201 | 15 |
| 1999-05-16 | vs BAL | 37 | L 5-16 | 21-16 | 1 | 39,508 | Aaron Sele | Sidney Ponson | Sidney Ponson | Aaron Sele | | 221 | 217 | 4 |
| 1999-05-17 | vs TBA | 38 | L 3-13 | 22-16 | 1 | 29,946 | John Burkett | Ryan Rupe | Ryan Rupe | John Burkett | | 224 | 230 | -6 |
| 1999-05-18 | vs TBA | 39 | L 4-5 | 22-17 | 1 | 29,706 | Mike Morgan | Rolando Arrojo | Rolando Arrojo | Mike Morgan | Roberto Hernandez | 228 | 235 | -7 |
| 1999-05-19 | vs TBA | 40 | W 7-6 | 23-17 | 1 | 29,513 | Mark Clark | Bobby Witt | Jeff Zimmerman | Scott Aldred | John Wetteland | 235 | 241 | -6 |
| 1999-05-21 | @ BAL | 41 | L 2-3 | 23-18 | 1 | 45,867 | Rick Helling | Sidney Ponson | Sidney Ponson | Rick Helling | | 237 | 244 | -7 |
| 1999-05-22 | @ BAL | 42 | W 8-7 | 24-18 | 1 | 47,915 | Aaron Sele | Juan Guzman | Tim Crabtree | Mike Timlin | John Wetteland | 245 | 251 | -6 |
| 1999-05-23 | @ BAL | 43 | L 6-15 | 25-18 | 1 | 40,516 | Mike Morgan | Mike Mussina | Mike Mussina | Mike Morgan | | 251 | 266 | -15 |
| 1999-05-24 | @ TBA | 44 | W 12-3 | 25-19 | 1 | 15,820 | Mark Clark | Rolando Arrojo | Mark Clark | Rolando Arrojo | | 263 | 269 | -6 |
| 1999-05-25 | @ TBA | 45 | W 7-2 | 26-19 | 1 | 16,058 | Ryan Glynn | Bobby Witt | Mike Venafro | Bobby Witt | | 270 | 271 | -1 |
| 1999-05-26 | @ TBA | 46 | W 8-6 | 27-19 | 1 | 17,575 | Rick Helling | Tony Saunders | Rick Helling | Julio Santana | John Wetteland | 278 | 277 | 1 |
| 1999-05-28 | vs MIN | 47 | W 6-4 | 28-19 | 1 | 27,765 | Aaron Sele | Brad Radke | Aaron Sele | Brad Radke | John Wetteland | 284 | 281 | 3 |
| 1999-05-29 | vs MIN | 48 | W 4-3 | 29-19 | 1 | 38,466 | John Burkett | Eric Milton | John Wetteland | Mike Trombley | | 288 | 284 | 4 |
| 1999-05-30 | vs MIN | 49 | W 3-2 | 30-19 | 1 | 40,286 | Mark Clark | Dan Perkins | Jeff Zimmerman | Joe Mays | John Wetteland | 291 | 286 | 5 |
| 1999-05-31 | vs KCA | 50 | W 4-3 | 31-19 | 1 | 28,962 | Ryan Glynn | Jeff Suppan | Tim Crabtree | Jose Santiago | | 295 | 289 | 6 |
| 1999-06-01 | vs KCA | 51 | W 3-1 | 32-19 | 1 | 25,184 | Rick Helling | Jay Witasick | Jeff Zimmerman | Matt Whisenant | John Wetteland | 298 | 290 | 8 |
| 1999-06-02 | vs KCA | 52 | W 7-4 | 33-19 | 1 | 32,598 | Aaron Sele | Kevin Appier | Aaron Sele | Kevin Appier | John Wetteland | 305 | 294 | 11 |
| 1999-06-04 | @ ARI | 53 | L 3-11 | 34-19 | 1 | 41,029 | Mark Clark | Randy Johnson | Randy Johnson | Mark Clark | | 308 | 305 | 3 |
| 1999-06-05 | @ ARI | 54 | W 9-8 | 35-19 | 1 | 41,820 | Ryan Glynn | Armando Reynoso | Mike Venafro | Darren Holmes | John Wetteland | 317 | 313 | 4 |
| 1999-06-06 | @ ARI | 55 | L 2-4 | 35-20 | 1 | 34,353 | Rick Helling | Andy Benes | Andy Benes | Rick Helling | Gregg Olson | 319 | 317 | 2 |
| 1999-06-07 | @ LAN | 56 | W 3-2 | 36-20 | 1 | 26,462 | Aaron Sele | Ismael Valdez | Aaron Sele | Ismael Valdez | John Wetteland | 322 | 319 | 3 |
| 1999-06-08 | @ LAN | 57 | W 7-6 | 37-20 | 1 | 26,255 | Mike Morgan | Darren Dreifort | Jeff Zimmerman | Alan Mills | Mike Munoz | 329 | 325 | 4 |
| 1999-06-09 | @ LAN | 58 | L 2-7 | 37-21 | 1 | 46,539 | Mark Clark | Kevin Brown | Kevin Brown | Mark Clark | | 331 | 332 | -1 |
| 1999-06-11 | vs COL | 59 | W 3-2 | 38-21 | 1 | 39,627 | Rick Helling | Darryl Kile | Jeff Zimmerman | Chuck McElroy | John Wetteland | 334 | 334 | 0 |
| 1999-06-12 | vs COL | 60 | L 7-8 | 38-22 | 1 | 46,851 | Aaron Sele | Pedro Astacio | Pedro Astacio | Aaron Sele | Dave Veres | 341 | 342 | -1 |
| 1999-06-13 | vs COL | 61 | L 2-4 | 38-23 | 1 | 39,651 | Mike Morgan | Bobby Jones | Bobby Jones | Mike Morgan | Dave Veres | 343 | 346 | -3 |
| 1999-06-14 | @ NYA | 62 | L 2-8 | 38-24 | 1 | 27,812 | Mark Clark | Hideki Irabu | Hideki Irabu | Mark Clark | | 345 | 354 | -9 |
| 1999-06-15 | @ NYA | 63 | L 2-6 | 38-25 | 1 | 28,200 | Ryan Glynn | David Cone | David Cone | Ryan Glynn | | 347 | 360 | -13 |
| 1999-06-16 | @ NYA | 64 | W 3-0 | 39-25 | 1 | 28,555 | Rick Helling | Orlando Hernandez | Rick Helling | Orlando Hernandez | John Wetteland | 350 | 360 | -10 |
| 1999-06-17 | @ NYA | 65 | W 4-2 | 40-25 | 1 | 30,157 | Aaron Sele | Roger Clemens | Aaron Sele | Roger Clemens | John Wetteland | 354 | 362 | -8 |
| 1999-06-18 | @ BOS | 66 | W 4-1 | 41-25 | 1 | 31,427 | Mike Morgan | Mark Portugal | Mike Morgan | Mark Portugal | Jeff Zimmerman | 358 | 363 | -5 |
| 1999-06-19 | @ BOS | 67 | L 4-7 | 41-26 | 1 | 31,950 | Mark Clark | Jin Ho Cho | Jin Ho Cho | Mark Clark | Tim Wakefield | 362 | 370 | -8 |
| 1999-06-20 | @ BOS | 68 | L 2-5 | 41-27 | 1 | 31,501 | Ryan Glynn | Pedro Martinez | Pedro Martinez | Ryan Glynn | Tim Wakefield | 364 | 375 | -11 |
| 1999-06-21 | @ BOS | 69 | L 4-5 | 41-28 | 1 | 27,627 | Rick Helling | Brian Rose | John Wasdin | Rick Helling | Tim Wakefield | 368 | 380 | -12 |
| 1999-06-22 | vs OAK | 70 | L 3-5 | 41-29 | 1 | 35,619 | Aaron Sele | Kenny Rogers | T.J. Mathews | John Wetteland | Billy Taylor | 371 | 385 | -14 |
| 1999-06-23 | vs OAK | 71 | W 7-6 | 42-29 | 1 | 45,995 | Mike Morgan | Mike Oquist | Mike Morgan | Mike Oquist | John Wetteland | 378 | 391 | -13 |
| 1999-06-24 | vs OAK | 72 | W 5-2 | 43-29 | 1 | 39,683 | John Burkett | Tim Hudson | John Burkett | Tim Hudson | John Wetteland | 383 | 393 | -10 |
| 1999-06-25 | @ SEA | 73 | W 14-4 | 43-30 | 1 | 30,490 | Ryan Glynn | Paul Abbott | Ryan Glynn | Frankie Rodriguez | | 397 | 397 | 0 |
| 1999-06-26 | @ SEA | 74 | L 4-5 | 43-31 | 1 | 37,992 | Rick Helling | Jamie Moyer | Jose Paniagua | Mike Venafro | Jose Mesa | 401 | 402 | -1 |
| 1999-06-27 | @ SEA | 75 | L 2-5 | 43-32 | 1 | 56,530 | Aaron Sele | Freddy Garcia | Freddy Garcia | Aaron Sele | Jose Mesa | 403 | 407 | -4 |
| 1999-06-28 | @ ANA | 76 | W 9-1 | 44-32 | 1 | 20,539 | Mike Morgan | Chuck Finley | Mike Morgan | Chuck Finley | | 412 | 408 | 4 |
| 1999-06-29 | @ ANA | 77 | W 5-0 | 45-32 | 1 | 22,274 | John Burkett | Omar Olivares | John Burkett | Omar Olivares | | 417 | 408 | 9 |
| 1999-06-30 | @ ANA | 78 | W 18-4 | 45-33 | 1 | 23,450 | Ryan Glynn | Ken Hill | Ryan Glynn | Ken Hill | | 435 | 412 | 23 |
| 1999-07-02 | vs SEA | 79 | W 7-6 | 46-33 | 1 | 39,677 | Rick Helling | Jamie Moyer | John Wetteland | Ken Cloude | | 442 | 418 | 24 |
| 1999-07-03 | vs SEA | 80 | L 12-13 | 46-34 | 1 | 46,674 | Aaron Sele | Freddy Garcia | Jose Paniagua | Tim Crabtree | Jose Mesa | 454 | 431 | 23 |
| 1999-07-04 | vs SEA | 81 | L 0-6 | 46-35 | 1 | 47,204 | Mike Morgan | John Halama | John Halama | Mike Morgan | | 454 | 437 | 17 |
| 1999-07-05 | @ OAK | 82 | L 2-4 | 46-36 | 1 | 7,490 | John Burkett | Tim Hudson | Tim Hudson | John Burkett | Billy Taylor | 456 | 441 | 15 |
| 1999-07-06 | @ OAK | 83 | L 0-4 | 46-37 | 1 | 8,221 | Ryan Glynn | Jimmy Haynes | Jimmy Haynes | Ryan Glynn | | 456 | 445 | 11 |
| 1999-07-07 | @ OAK | 84 | W 7-4 | 47-37 | 1 | 15,566 | Rick Helling | Kenny Rogers | Jeff Zimmerman | Brad Rigby | John Wetteland | 463 | 449 | 14 |
| 1999-07-09 | @ SDN | 85 | W 7-2 | 48-37 | 1 | 25,546 | Aaron Sele | Woody Williams | Aaron Sele | Woody Williams | | 470 | 451 | 19 |
| 1999-07-10 | @ SDN | 86 | L 4-5 | 48-38 | 1 | 49,123 | Mike Morgan | Andy Ashby | Donne Wall | John Wetteland | | 474 | 456 | 18 |
| 1999-07-11 | @ SDN | 87 | L 2-6 | 48-39 | 1 | 31,301 | John Burkett | Matt Clement | Dan Miceli | Esteban Loaiza | | 476 | 462 | 14 |
| 1999-07-15 | vs ARI | 88 | W 3-2 | 49-39 | 1 | 33,328 | Rick Helling | Randy Johnson | Mike Venafro | Matt Mantei | | 479 | 464 | 15 |
| 1999-07-16 | vs ARI | 89 | W 9-8 | 50-39 | 1 | 38,802 | Aaron Sele | Armando Reynoso | John Wetteland | Bobby Chouinard | | 488 | 472 | 16 |
| 1999-07-17 | vs ARI | 90 | L 6-8 | 50-40 | 1 | 34,421 | John Burkett | Andy Benes | Dan Plesac | John Wetteland | Matt Mantei | 494 | 480 | 14 |
| 1999-07-18 | vs SFN | 91 | W 5-4 | 51-40 | 1 | 41,746 | Mike Morgan | Mark Gardner | Mike Morgan | Mark Gardner | John Wetteland | 499 | 484 | 15 |
| 1999-07-19 | vs SFN | 92 | W 14-7 | 51-41 | 1 | 40,976 | Ryan Glynn | Chris Brock | Esteban Loaiza | Chris Brock | | 513 | 491 | 22 |
| 1999-07-20 | vs SFN | 93 | W 6-3 | 52-41 | 1 | 33,922 | Rick Helling | Shawn Estes | Rick Helling | Shawn Estes | | 519 | 494 | 25 |
| 1999-07-21 | vs ANA | 94 | W 9-5 | 53-41 | 1 | 35,849 | Aaron Sele | Omar Olivares | Aaron Sele | Omar Olivares | Jeff Zimmerman | 528 | 499 | 29 |
| 1999-07-22 | vs ANA | 95 | W 9-7 | 54-41 | 1 | 31,101 | John Burkett | Steve Sparks | John Burkett | Steve Sparks | Jeff Zimmerman | 537 | 506 | 31 |
| 1999-07-23 | @ TBA | 96 | W 11-8 | 54-42 | 1 | 18,960 | Mike Morgan | Ryan Rupe | Danny Kolb | Ryan Rupe | | 548 | 514 | 34 |
| 1999-07-24 | @ TBA | 97 | W 5-3 | 55-42 | 1 | 22,780 | Esteban Loaiza | Dave Eiland | Esteban Loaiza | Alan Newman | John Wetteland | 553 | 517 | 36 |
| 1999-07-25 | @ TBA | 98 | W 4-3 | 56-42 | 1 | 21,202 | Rick Helling | Rolando Arrojo | Rick Helling | Rolando Arrojo | John Wetteland | 557 | 520 | 37 |
| 1999-07-27 | @ BAL | 99 | W 8-6 | 57-42 | 1 | 42,949 | Aaron Sele | Mike Mussina | Aaron Sele | Mike Mussina | John Wetteland | 565 | 526 | 39 |
| 1999-07-28 | @ BAL | 100 | L 6-8 | 57-43 | 1 | 41,692 | John Burkett | Scott Erickson | Scott Erickson | John Burkett | Mike Timlin | 571 | 534 | 37 |
| 1999-07-29 | @ BAL | 101 | W 3-1 | 58-43 | 1 | 43,711 | Mike Morgan | Juan Guzman | Mike Morgan | Juan Guzman | John Wetteland | 574 | 535 | 39 |
| 1999-07-30 | vs KCA | 102 | W 9-2 | 59-43 | 1 | 39,611 | Esteban Loaiza | Jay Witasick | Esteban Loaiza | Jay Witasick | | 583 | 537 | 46 |
| 1999-07-31 | vs KCA | 103 | L 8-12 | 60-43 | 1 | 46,549 | Rick Helling | Dan Reichert | Dan Reichert | Mike Munoz | Scott Service | 591 | 549 | 42 |
| 1999-08-01 | vs KCA | 104 | W 12-5 | 60-44 | 1 | 31,698 | Aaron Sele | Brian Barber | Aaron Sele | Brian Barber | | 603 | 554 | 49 |
| 1999-08-02 | vs MIN | 105 | W 5-4 | 61-44 | 1 | 24,720 | John Burkett | LaTroy Hawkins | Jeff Zimmerman | Eddie Guardado | John Wetteland | 608 | 558 | 50 |
| 1999-08-03 | vs MIN | 106 | W 9-5 | 62-44 | 1 | 28,090 | Mike Morgan | Benj Sampson | Mike Morgan | Benj Sampson | | 617 | 563 | 54 |
| 1999-08-04 | vs MIN | 107 | W 3-1 | 63-44 | 1 | 29,224 | Esteban Loaiza | Brad Radke | Esteban Loaiza | Brad Radke | John Wetteland | 620 | 564 | 56 |
| 1999-08-06 | vs TOR | 108 | L 4-5 | 63-45 | 1 | 31,664 | Rick Helling | Chris Carpenter | Chris Carpenter | Jeff Zimmerman | Billy Koch | 624 | 569 | 55 |
| 1999-08-07 | vs TOR | 109 | W 6-0 | 64-45 | 1 | 40,329 | Aaron Sele | Pat Hentgen | Aaron Sele | Pat Hentgen | | 630 | 569 | 61 |
| 1999-08-08 | vs TOR | 110 | L 7-8 | 64-46 | 1 | 32,374 | John Burkett | David Wells | John Frascatore | Mike Venafro | Billy Koch | 637 | 577 | 60 |
| 1999-08-09 | vs TOR | 111 | L 4-19 | 65-46 | 1 | 23,235 | Mike Morgan | Joey Hamilton | Joey Hamilton | Mike Morgan | | 641 | 596 | 45 |
| 1999-08-10 | vs DET | 112 | W 4-3 | 66-46 | 1 | 24,398 | Esteban Loaiza | Justin Thompson | Danny Patterson | Nelson Cruz | | 645 | 599 | 46 |
| 1999-08-11 | vs DET | 113 | W 8-2 | 67-46 | 1 | 27,432 | Rick Helling | Willie Blair | Rick Helling | Willie Blair | | 653 | 601 | 52 |
| 1999-08-12 | vs DET | 114 | L 1-3 | 67-47 | 1 | 27,209 | Aaron Sele | Dave Mlicki | Dave Mlicki | Aaron Sele | Todd Jones | 654 | 604 | 50 |
| 1999-08-13 | @ CHA | 115 | L 2-4 | 67-49 | 2 | 0 | John Burkett | Kip Wells | Kip Wells | John Burkett | Bob Howry | 656 | 608 | 48 |
| 1999-08-13 | @ CHA | 116 | L 4-7 | 67-49 | 2 | 20,444 | Ryan Glynn | James Baldwin | James Baldwin | Ryan Glynn | | 660 | 615 | 45 |
| 1999-08-14 | @ CHA | 117 | L 7-8 | 67-50 | 1 | 27,476 | Mike Morgan | Jim Parque | Bob Howry | Jeff Zimmerman | | 667 | 623 | 44 |
| 1999-08-15 | @ CHA | 118 | W 10-0 | 68-50 | 1 | 22,708 | Esteban Loaiza | John Snyder | Esteban Loaiza | John Snyder | | 677 | 623 | 54 |
| 1999-08-16 | @ CLE | 119 | W 13-5 | 68-51 | 1 | 43,226 | Rick Helling | Dave Burba | Mike Munoz | Ricardo Rincon | | 690 | 628 | 62 |
| 1999-08-17 | @ CLE | 120 | W 15-4 | 68-52 | 1 | 42,987 | Aaron Sele | Mark Langston | Aaron Sele | Mark Langston | | 705 | 632 | 73 |
| 1999-08-18 | @ CLE | 121 | W 6-1 | 69-52 | 1 | 42,997 | John Burkett | Charles Nagy | John Burkett | Charles Nagy | | 711 | 633 | 78 |
| 1999-08-19 | @ CLE | 122 | L 0-8 | 69-53 | 2 | 43,263 | Mike Morgan | Steve Karsay | Steve Karsay | Mike Morgan | | 711 | 641 | 70 |
| 1999-08-20 | vs BOS | 123 | W 4-3 | 70-53 | 1 | 35,036 | Esteban Loaiza | Mark Portugal | Esteban Loaiza | Mark Portugal | John Wetteland | 715 | 644 | 71 |
| 1999-08-21 | vs BOS | 124 | W 9-2 | 71-53 | 1 | 45,641 | Rick Helling | Brian Rose | Rick Helling | Brian Rose | | 724 | 646 | 78 |
| 1999-08-22 | vs BOS | 125 | W 6-0 | 72-53 | 1 | 28,099 | Aaron Sele | Tim Wakefield | Aaron Sele | Tim Wakefield | | 730 | 646 | 84 |
| 1999-08-23 | vs NYA | 126 | L 3-21 | 73-53 | 1 | 38,024 | John Burkett | Andy Pettitte | Andy Pettitte | John Burkett | | 733 | 667 | 66 |
| 1999-08-24 | vs NYA | 127 | L 7-10 | 74-53 | 1 | 39,727 | Mike Morgan | David Cone | Ramiro Mendoza | Corey Lee | Mariano Rivera | 740 | 677 | 63 |
| 1999-08-25 | vs NYA | 128 | W 7-3 | 75-53 | 1 | 38,345 | Esteban Loaiza | Hideki Irabu | Esteban Loaiza | Hideki Irabu | | 747 | 680 | 67 |
| 1999-08-27 | @ TOR | 129 | W 8-2 | 76-53 | 1 | 30,181 | Rick Helling | Chris Carpenter | Rick Helling | Chris Carpenter | | 755 | 682 | 73 |
| 1999-08-28 | @ TOR | 130 | W 9-7 | 77-53 | 1 | 31,117 | Aaron Sele | David Wells | Aaron Sele | David Wells | John Wetteland | 764 | 689 | 75 |
| 1999-08-29 | @ TOR | 131 | W 4-2 | 78-53 | 1 | 30,502 | John Burkett | Roy Halladay | John Burkett | Roy Halladay | John Wetteland | 768 | 691 | 77 |
| 1999-08-30 | @ DET | 132 | L 0-1 | 78-54 | 1 | 19,007 | Esteban Loaiza | Brian Moehler | Brian Moehler | Esteban Loaiza | | 768 | 692 | 76 |
| 1999-08-31 | @ DET | 133 | L 6-14 | 79-54 | 1 | 17,439 | Mike Morgan | Dave Borkowski | Francisco Cordero | Danny Kolb | | 774 | 706 | 68 |
| 1999-09-01 | @ DET | 134 | W 14-7 | 79-55 | 1 | 18,544 | Rick Helling | Jeff Weaver | Rick Helling | Jeff Weaver | John Wetteland | 788 | 713 | 75 |
| 1999-09-02 | @ DET | 135 | L 7-8 | 79-56 | 1 | 22,945 | Aaron Sele | Dave Mlicki | Dave Mlicki | Jeff Zimmerman | Todd Jones | 795 | 721 | 74 |
| 1999-09-03 | vs CHA | 136 | W 10-4 | 79-57 | 1 | 29,266 | John Burkett | James Baldwin | John Burkett | James Baldwin | | 805 | 725 | 80 |
| 1999-09-04 | vs CHA | 137 | L 3-12 | 80-57 | 1 | 29,279 | Esteban Loaiza | Jaime Navarro | Carlos Castillo | Esteban Loaiza | | 808 | 737 | 71 |
| 1999-09-06 | vs CHA | 138 | W 8-6 | 81-57 | 2 | 0 | Rick Helling | Jim Parque | Rick Helling | Jim Parque | John Wetteland | 816 | 743 | 73 |
| 1999-09-06 | vs CHA | 139 | W 6-3 | 81-57 | 2 | 31,443 | Jeff Fassero | John Snyder | Jeff Fassero | John Snyder | John Wetteland | 822 | 746 | 76 |
| 1999-09-07 | vs CLE | 140 | W 4-3 | 83-57 | 1 | 26,011 | Aaron Sele | Charles Nagy | Aaron Sele | Steve Reed | John Wetteland | 826 | 749 | 77 |
| 1999-09-08 | vs CLE | 141 | W 3-0 | 84-57 | 1 | 29,889 | John Burkett | Chris Haney | John Burkett | Chris Haney | John Wetteland | 829 | 749 | 80 |
| 1999-09-10 | @ KCA | 142 | L 3-7 | 84-58 | 1 | 14,234 | Esteban Loaiza | Blake Stein | Blake Stein | Esteban Loaiza | Jeff Montgomery | 832 | 756 | 76 |
| 1999-09-11 | @ KCA | 143 | L 6-9 | 84-59 | 1 | 24,683 | Rick Helling | Jeff Suppan | Jeff Suppan | Rick Helling | Jeff Montgomery | 838 | 765 | 73 |
| 1999-09-12 | @ KCA | 144 | L 3-6 | 84-60 | 1 | 12,590 | Aaron Sele | Jay Witasick | Jay Witasick | Aaron Sele | Alvin Morman | 841 | 771 | 70 |
| 1999-09-13 | @ KCA | 145 | W 8-4 | 85-60 | 1 | 11,643 | John Burkett | Jose Rosado | John Wetteland | Jose Santiago | | 849 | 775 | 74 |
| 1999-09-14 | @ MIN | 146 | W 5-4 | 86-60 | 1 | 9,717 | Jeff Fassero | Jason Ryan | Danny Kolb | Eddie Guardado | John Wetteland | 854 | 779 | 75 |
| 1999-09-15 | @ MIN | 147 | W 8-3 | 87-60 | 1 | 9,706 | Esteban Loaiza | Brad Radke | Esteban Loaiza | Brad Radke | | 862 | 782 | 80 |
| 1999-09-17 | vs TBA | 148 | L 5-7 | 87-61 | 1 | 33,695 | Rick Helling | Dan Wheeler | Alan Newman | Rick Helling | Roberto Hernandez | 867 | 789 | 78 |
| 1999-09-18 | vs TBA | 149 | W 6-1 | 88-61 | 1 | 36,820 | Aaron Sele | Bobby Witt | Aaron Sele | Bobby Witt | | 873 | 790 | 83 |
| 1999-09-19 | vs TBA | 150 | L 2-15 | 89-61 | 1 | 24,930 | John Burkett | Rolando Arrojo | Rolando Arrojo | John Burkett | | 875 | 805 | 70 |
| 1999-09-21 | vs BAL | 151 | L 2-4 | 89-62 | 1 | 24,192 | Esteban Loaiza | Jason Johnson | Jason Johnson | Esteban Loaiza | Mike Timlin | 877 | 809 | 68 |
| 1999-09-22 | vs BAL | 152 | L 4-7 | 89-63 | 1 | 34,007 | Rick Helling | Scott Erickson | Scott Erickson | Rick Helling | Mike Timlin | 881 | 816 | 65 |
| 1999-09-24 | vs OAK | 153 | W 12-4 | 89-64 | 1 | 40,207 | Aaron Sele | Gil Heredia | Aaron Sele | Gil Heredia | | 893 | 820 | 73 |
| 1999-09-25 | vs OAK | 154 | W 10-4 | 89-65 | 1 | 46,178 | John Burkett | Kevin Appier | John Burkett | Kevin Appier | | 903 | 824 | 79 |
| 1999-09-26 | vs OAK | 155 | W 10-3 | 89-66 | 1 | 38,656 | Esteban Loaiza | Kevin Jarvis | Esteban Loaiza | Kevin Jarvis | | 913 | 827 | 86 |
| 1999-09-27 | vs SEA | 156 | W 3-2 | 90-66 | 1 | 32,118 | Rick Helling | Freddy Garcia | Tim Crabtree | Steve Sinclair | John Wetteland | 916 | 829 | 87 |
| 1999-09-28 | vs SEA | 157 | W 10-0 | 91-66 | 1 | 30,292 | Jeff Fassero | John Halama | Mike Morgan | John Halama | | 926 | 829 | 97 |
| 1999-09-29 | vs SEA | 158 | L 3-7 | 91-67 | 1 | 39,474 | Aaron Sele | Gil Meche | Gil Meche | Aaron Sele | | 929 | 836 | 93 |
| 1999-09-30 | vs SEA | 159 | W 7-0 | 92-67 | 1 | 28,214 | John Burkett | Brett Hinchliffe | John Burkett | Brett Hinchliffe | | 936 | 836 | 100 |
| 1999-10-01 | @ ANA | 160 | L 6-7 | 92-68 | 1 | 25,515 | Esteban Loaiza | Ramon Ortiz | Mike Holtz | Mike Morgan | | 942 | 843 | 99 |
| 1999-10-02 | @ ANA | 161 | L 3-15 | 93-68 | 1 | 33,239 | Rick Helling | Al Levine | Shigetoshi Hasegawa | Rick Helling | | 945 | 858 | 87 |
| 1999-10-03 | @ ANA | 162 | L 0-1 | 93-69 | 1 | 23,556 | Matt Perisho | Jarrod Washburn | Jarrod Washburn | Mike Morgan | Lou Pote | 945 | 859 | 86 |