| 1999-04-05 | @ OAK | 1 | L 3-5 | 0-1 | 4 | 46,380 | Roger Clemens | Gil Heredia | T.J. Mathews | Mike Stanton | | 3 | 5 | -2 |
| 1999-04-06 | @ OAK | 2 | W 7-4 | 1-1 | 3 | 15,579 | Orlando Hernandez | Tom Candiotti | Orlando Hernandez | Tom Candiotti | Mariano Rivera | 10 | 9 | 1 |
| 1999-04-07 | @ OAK | 3 | W 4-0 | 2-1 | 3 | 18,846 | Ramiro Mendoza | Jimmy Haynes | Ramiro Mendoza | Jimmy Haynes | | 14 | 9 | 5 |
| 1999-04-09 | vs DET | 4 | W 12-3 | 2-2 | 4 | 56,583 | David Cone | Beiker Graterol | David Cone | Beiker Graterol | | 26 | 12 | 14 |
| 1999-04-10 | vs DET | 5 | W 5-0 | 3-2 | 2 | 42,058 | Roger Clemens | Brian Moehler | Roger Clemens | Brian Moehler | | 31 | 12 | 19 |
| 1999-04-11 | vs DET | 6 | W 11-2 | 3-3 | 4 | 32,398 | Orlando Hernandez | Justin Thompson | Orlando Hernandez | Justin Thompson | | 42 | 14 | 28 |
| 1999-04-13 | vs BAL | 7 | W 6-3 | 4-3 | 4 | 25,254 | Ramiro Mendoza | Juan Guzman | Jeff Nelson | Arthur Rhodes | | 48 | 17 | 31 |
| 1999-04-14 | vs BAL | 8 | W 14-7 | 4-4 | 4 | 26,898 | David Cone | Scott Erickson | David Cone | Scott Erickson | | 62 | 24 | 38 |
| 1999-04-15 | vs BAL | 9 | L 7-9 | 4-5 | 4 | 30,958 | Roger Clemens | Mike Mussina | Arthur Rhodes | Mariano Rivera | Mike Timlin | 69 | 33 | 36 |
| 1999-04-16 | @ DET | 10 | L 1-8 | 4-6 | 4 | 14,816 | Orlando Hernandez | Justin Thompson | Justin Thompson | Orlando Hernandez | | 70 | 41 | 29 |
| 1999-04-17 | @ DET | 11 | L 1-3 | 4-7 | 4 | 17,821 | Andy Pettitte | Willie Blair | Matt Anderson | Jeff Nelson | Todd Jones | 71 | 44 | 27 |
| 1999-04-18 | @ DET | 12 | L 1-5 | 4-8 | 4 | 16,503 | Ramiro Mendoza | Dave Mlicki | Dave Mlicki | Ramiro Mendoza | | 72 | 49 | 23 |
| 1999-04-20 | vs TEX | 13 | W 4-0 | 5-8 | 4 | 24,514 | David Cone | John Burkett | David Cone | John Burkett | | 76 | 49 | 27 |
| 1999-04-21 | vs TEX | 14 | W 4-2 | 6-8 | 4 | 23,984 | Roger Clemens | Rick Helling | Roger Clemens | Rick Helling | Mariano Rivera | 80 | 51 | 29 |
| 1999-04-23 | vs TOR | 15 | W 6-4 | 7-8 | 4 | 36,529 | Orlando Hernandez | David Wells | Orlando Hernandez | David Wells | Mariano Rivera | 86 | 55 | 31 |
| 1999-04-24 | vs TOR | 16 | W 7-4 | 8-8 | 4 | 46,924 | Andy Pettitte | Roy Halladay | Ramiro Mendoza | Dan Plesac | Mariano Rivera | 93 | 59 | 34 |
| 1999-04-25 | vs TOR | 17 | W 4-3 | 9-8 | 4 | 51,903 | David Cone | Kelvim Escobar | Jason Grimsley | Robert Person | | 97 | 62 | 35 |
| 1999-04-27 | @ TEX | 18 | W 7-6 | 10-8 | 2 | 42,690 | Roger Clemens | Aaron Sele | Mike Stanton | John Wetteland | Mariano Rivera | 104 | 68 | 36 |
| 1999-04-28 | @ TEX | 19 | L 6-8 | 10-9 | 4 | 33,038 | Orlando Hernandez | Mark Clark | Mike Munoz | Mike Stanton | John Wetteland | 110 | 76 | 34 |
| 1999-04-29 | @ TEX | 20 | W 5-3 | 11-9 | 3 | 35,573 | Ramiro Mendoza | Mike Morgan | Ramiro Mendoza | Mike Morgan | Mariano Rivera | 115 | 79 | 36 |
| 1999-04-30 | @ KCA | 21 | L 6-13 | 12-9 | 2 | 29,054 | Andy Pettitte | Jay Witasick | Alvin Morman | Andy Pettitte | | 121 | 92 | 29 |
| 1999-05-01 | @ KCA | 22 | W 8-4 | 13-9 | 2 | 29,692 | David Cone | Jim Pittsley | David Cone | Jim Pittsley | | 129 | 96 | 33 |
| 1999-05-02 | @ KCA | 23 | W 9-8 | 14-9 | 2 | 24,666 | Hideki Irabu | Kevin Appier | Jason Grimsley | Jose Santiago | Mariano Rivera | 138 | 104 | 34 |
| 1999-05-03 | @ KCA | 24 | L 3-9 | 14-10 | 2 | 18,021 | Orlando Hernandez | Jose Rosado | Scott Service | Orlando Hernandez | | 141 | 113 | 28 |
| 1999-05-04 | @ MIN | 25 | L 5-8 | 14-11 | 2 | 15,923 | Ramiro Mendoza | Mike Lincoln | Mike Lincoln | Ramiro Mendoza | Rick Aguilera | 146 | 121 | 25 |
| 1999-05-05 | @ MIN | 26 | W 5-3 | 15-11 | 2 | 17,859 | Andy Pettitte | LaTroy Hawkins | Andy Pettitte | LaTroy Hawkins | Mariano Rivera | 151 | 124 | 27 |
| 1999-05-06 | @ MIN | 27 | W 4-3 | 16-11 | 2 | 16,465 | David Cone | Brad Radke | Jason Grimsley | Rick Aguilera | Mariano Rivera | 155 | 127 | 28 |
| 1999-05-07 | vs SEA | 28 | W 10-1 | 17-11 | 2 | 38,476 | Hideki Irabu | Mac Suzuki | Hideki Irabu | Mac Suzuki | | 165 | 128 | 37 |
| 1999-05-08 | vs SEA | 29 | L 5-14 | 18-11 | 1 | 41,786 | Orlando Hernandez | Freddy Garcia | Freddy Garcia | Orlando Hernandez | | 170 | 142 | 28 |
| 1999-05-09 | vs SEA | 30 | W 6-1 | 19-11 | 1 | 49,622 | Mike Stanton | Jeff Fassero | Jason Grimsley | Jeff Fassero | | 176 | 143 | 33 |
| 1999-05-11 | vs ANA | 31 | L 7-9 | 19-12 | 2 | 25,313 | Andy Pettitte | Steve Sparks | Mark Petkovsek | Ramiro Mendoza | Troy Percival | 183 | 152 | 31 |
| 1999-05-12 | vs ANA | 32 | L 0-1 | 19-13 | 2 | 23,540 | David Cone | Chuck Finley | Chuck Finley | David Cone | Troy Percival | 183 | 153 | 30 |
| 1999-05-13 | vs ANA | 33 | L 0-2 | 19-14 | 2 | 26,702 | Hideki Irabu | Omar Olivares | Omar Olivares | Hideki Irabu | Troy Percival | 183 | 155 | 28 |
| 1999-05-14 | vs CHA | 34 | L 2-8 | 19-15 | 3 | 33,793 | Orlando Hernandez | Jim Parque | Jim Parque | Orlando Hernandez | Bill Simas | 185 | 163 | 22 |
| 1999-05-15 | vs CHA | 35 | L 4-12 | 20-15 | 3 | 45,824 | Ramiro Mendoza | John Snyder | John Snyder | Ramiro Mendoza | | 189 | 175 | 14 |
| 1999-05-16 | vs CHA | 36 | W 2-1 | 21-15 | 2 | 51,046 | Andy Pettitte | Mike Sirotka | Andy Pettitte | Mike Sirotka | Mariano Rivera | 191 | 176 | 15 |
| 1999-05-18 | @ BOS | 37 | L 3-6 | 21-16 | 3 | 33,620 | David Cone | Pedro Martinez | Pedro Martinez | David Cone | Tom Gordon | 194 | 182 | 12 |
| 1999-05-19 | @ BOS | 38 | L 0-6 | 21-17 | 3 | 32,091 | Hideki Irabu | Brian Rose | Brian Rose | Hideki Irabu | | 194 | 188 | 6 |
| 1999-05-20 | @ BOS | 39 | W 3-1 | 22-17 | 3 | 33,139 | Orlando Hernandez | Mark Portugal | Orlando Hernandez | Mark Portugal | Mariano Rivera | 197 | 189 | 8 |
| 1999-05-22 | @ CHA | 40 | W 10-2 | 22-19 | 4 | 0 | Roger Clemens | John Snyder | Roger Clemens | John Snyder | | 207 | 191 | 16 |
| 1999-05-22 | @ CHA | 41 | L 1-2 | 22-19 | 4 | 35,310 | Andy Pettitte | Mike Sirotka | Mike Sirotka | Andy Pettitte | Bill Simas | 208 | 193 | 15 |
| 1999-05-23 | @ CHA | 42 | W 8-7 | 23-19 | 3 | 22,845 | David Cone | Jaime Navarro | Mariano Rivera | Bill Simas | | 216 | 200 | 16 |
| 1999-05-25 | vs BOS | 43 | L 2-5 | 23-20 | 3 | 37,715 | Hideki Irabu | Brian Rose | Brian Rose | Hideki Irabu | Tom Gordon | 218 | 205 | 13 |
| 1999-05-26 | vs BOS | 44 | W 8-3 | 24-20 | 3 | 45,800 | Orlando Hernandez | Mark Portugal | Orlando Hernandez | Mark Portugal | Mariano Rivera | 226 | 208 | 18 |
| 1999-05-27 | vs BOS | 45 | W 4-1 | 25-20 | 3 | 27,631 | Roger Clemens | Pat Rapp | Roger Clemens | Pat Rapp | Mariano Rivera | 230 | 209 | 21 |
| 1999-05-28 | @ TOR | 46 | W 10-6 | 25-21 | 3 | 30,355 | Andy Pettitte | Chris Carpenter | Andy Pettitte | Chris Carpenter | | 240 | 215 | 25 |
| 1999-05-29 | @ TOR | 47 | W 8-3 | 26-21 | 3 | 40,175 | David Cone | Pat Hentgen | David Cone | Pat Hentgen | | 248 | 218 | 30 |
| 1999-05-30 | @ TOR | 48 | W 8-3 | 27-21 | 2 | 39,111 | Hideki Irabu | David Wells | Hideki Irabu | David Wells | | 256 | 221 | 35 |
| 1999-05-31 | vs CLE | 49 | L 1-7 | 27-22 | 3 | 46,605 | Orlando Hernandez | Charles Nagy | Charles Nagy | Orlando Hernandez | | 257 | 228 | 29 |
| 1999-06-01 | vs CLE | 50 | W 11-5 | 27-23 | 3 | 32,759 | Roger Clemens | Dave Burba | Roger Clemens | Dave Burba | | 268 | 233 | 35 |
| 1999-06-02 | vs CLE | 51 | L 7-10 | 28-23 | 3 | 36,955 | Andy Pettitte | Jaret Wright | Steve Karsay | Andy Pettitte | Michael Jackson | 275 | 243 | 32 |
| 1999-06-04 | vs NYN | 52 | W 4-3 | 29-23 | 3 | 56,175 | David Cone | Rick Reed | Jason Grimsley | Rick Reed | Mariano Rivera | 279 | 246 | 33 |
| 1999-06-05 | vs NYN | 53 | W 6-3 | 30-23 | 2 | 55,935 | Orlando Hernandez | Masato Yoshii | Orlando Hernandez | Masato Yoshii | Mariano Rivera | 285 | 249 | 36 |
| 1999-06-06 | vs NYN | 54 | L 2-7 | 30-24 | 3 | 56,294 | Roger Clemens | Al Leiter | Al Leiter | Roger Clemens | | 287 | 256 | 31 |
| 1999-06-07 | @ PHI | 55 | L 5-6 | 30-25 | 3 | 37,180 | Andy Pettitte | Paul Byrd | Paul Byrd | Andy Pettitte | | 292 | 262 | 30 |
| 1999-06-08 | @ PHI | 56 | L 5-11 | 31-25 | 2 | 44,444 | Hideki Irabu | Curt Schilling | Yorkis Perez | Jason Grimsley | | 297 | 273 | 24 |
| 1999-06-09 | @ PHI | 57 | W 11-5 | 31-26 | 2 | 42,047 | David Cone | Chad Ogea | David Cone | Chad Ogea | | 308 | 278 | 30 |
| 1999-06-11 | @ FLO | 58 | W 8-4 | 32-26 | 1 | 40,161 | Orlando Hernandez | Brian Meadows | Orlando Hernandez | Brian Meadows | Mariano Rivera | 316 | 282 | 34 |
| 1999-06-12 | @ FLO | 59 | W 5-4 | 33-26 | 1 | 42,110 | Roger Clemens | Livan Hernandez | Roger Clemens | Livan Hernandez | Mariano Rivera | 321 | 286 | 35 |
| 1999-06-13 | @ FLO | 60 | L 2-8 | 33-27 | 1 | 39,639 | Andy Pettitte | Alex Fernandez | Alex Fernandez | Andy Pettitte | | 323 | 294 | 29 |
| 1999-06-14 | vs TEX | 61 | W 8-2 | 34-27 | 1 | 27,812 | Hideki Irabu | Mark Clark | Hideki Irabu | Mark Clark | | 331 | 296 | 35 |
| 1999-06-15 | vs TEX | 62 | W 6-2 | 35-27 | 1 | 28,200 | David Cone | Ryan Glynn | David Cone | Ryan Glynn | | 337 | 298 | 39 |
| 1999-06-16 | vs TEX | 63 | L 0-3 | 35-28 | 1 | 28,555 | Orlando Hernandez | Rick Helling | Rick Helling | Orlando Hernandez | John Wetteland | 337 | 301 | 36 |
| 1999-06-17 | vs TEX | 64 | L 2-4 | 35-29 | 2 | 30,157 | Roger Clemens | Aaron Sele | Aaron Sele | Roger Clemens | John Wetteland | 339 | 305 | 34 |
| 1999-06-18 | vs ANA | 65 | W 4-1 | 36-29 | 1 | 39,996 | Andy Pettitte | Chuck Finley | Andy Pettitte | Chuck Finley | Mariano Rivera | 343 | 306 | 37 |
| 1999-06-19 | vs ANA | 66 | W 6-2 | 37-29 | 1 | 49,408 | Hideki Irabu | Omar Olivares | Hideki Irabu | Omar Olivares | Ramiro Mendoza | 349 | 308 | 41 |
| 1999-06-20 | vs ANA | 67 | L 2-4 | 37-30 | 2 | 55,626 | David Cone | Tim Belcher | Tim Belcher | David Cone | Troy Percival | 351 | 312 | 39 |
| 1999-06-22 | @ TBA | 68 | W 7-0 | 38-30 | 1 | 30,290 | Orlando Hernandez | Bobby Witt | Orlando Hernandez | Bobby Witt | | 358 | 312 | 46 |
| 1999-06-23 | @ TBA | 69 | W 12-4 | 38-31 | 1 | 30,474 | Roger Clemens | Dave Eiland | Roger Clemens | Dave Eiland | | 370 | 316 | 54 |
| 1999-06-24 | @ TBA | 70 | W 7-3 | 39-31 | 1 | 30,499 | Andy Pettitte | Bryan Rekar | Andy Pettitte | Bryan Rekar | Ramiro Mendoza | 377 | 319 | 58 |
| 1999-06-25 | @ BAL | 71 | W 9-8 | 40-31 | 1 | 47,936 | Hideki Irabu | Scott Erickson | Dan Naulty | Mike Timlin | Mariano Rivera | 386 | 327 | 59 |
| 1999-06-26 | @ BAL | 72 | W 7-4 | 41-31 | 1 | 47,841 | David Cone | Jason Johnson | David Cone | Jason Johnson | Mariano Rivera | 393 | 331 | 62 |
| 1999-06-27 | @ BAL | 73 | W 6-2 | 42-31 | 1 | 48,020 | Orlando Hernandez | Sidney Ponson | Orlando Hernandez | Sidney Ponson | | 399 | 333 | 66 |
| 1999-06-29 | vs DET | 74 | W 3-0 | 43-31 | 1 | 31,338 | Roger Clemens | Justin Thompson | Roger Clemens | Justin Thompson | | 402 | 333 | 69 |
| 1999-06-30 | vs DET | 75 | L 2-8 | 43-32 | 1 | 39,749 | Andy Pettitte | Brian Moehler | Brian Moehler | Andy Pettitte | | 404 | 341 | 63 |
| 1999-07-01 | vs DET | 76 | W 6-0 | 44-32 | 1 | 26,311 | Hideki Irabu | Dave Mlicki | Hideki Irabu | Dave Mlicki | | 410 | 341 | 69 |
| 1999-07-02 | vs BAL | 77 | W 2-1 | 45-32 | 1 | 37,518 | David Cone | Jason Johnson | David Cone | Jason Johnson | Mariano Rivera | 412 | 342 | 70 |
| 1999-07-03 | vs BAL | 78 | W 6-5 | 46-32 | 1 | 42,859 | Orlando Hernandez | Sidney Ponson | Jason Grimsley | Arthur Rhodes | | 418 | 347 | 71 |
| 1999-07-04 | vs BAL | 79 | L 3-7 | 46-33 | 1 | 37,046 | Roger Clemens | Juan Guzman | Juan Guzman | Ramiro Mendoza | Scott Kamieniecki | 421 | 354 | 67 |
| 1999-07-05 | vs BAL | 80 | L 1-9 | 46-34 | 2 | 29,934 | Andy Pettitte | Mike Mussina | Mike Mussina | Andy Pettitte | | 422 | 363 | 59 |
| 1999-07-06 | @ DET | 81 | W 9-8 | 47-34 | 1 | 23,785 | Hideki Irabu | Brian Moehler | Mariano Rivera | Todd Jones | Ramiro Mendoza | 431 | 371 | 60 |
| 1999-07-07 | @ DET | 82 | L 4-6 | 47-35 | 1 | 28,844 | David Cone | Dave Mlicki | Dave Mlicki | David Cone | Doug Brocail | 435 | 377 | 58 |
| 1999-07-08 | @ DET | 83 | W 3-2 | 48-35 | 1 | 34,417 | Orlando Hernandez | Jeff Weaver | Orlando Hernandez | C.J. Nitkowski | Mariano Rivera | 438 | 379 | 59 |
| 1999-07-09 | @ NYN | 84 | L 2-5 | 48-36 | 1 | 53,820 | Roger Clemens | Al Leiter | Al Leiter | Roger Clemens | Armando Benitez | 440 | 384 | 56 |
| 1999-07-10 | @ NYN | 85 | L 8-9 | 48-37 | 1 | 53,792 | Andy Pettitte | Rick Reed | Pat Mahomes | Mariano Rivera | | 448 | 393 | 55 |
| 1999-07-11 | @ NYN | 86 | W 6-3 | 49-37 | 1 | 53,869 | Hideki Irabu | Orel Hershiser | Hideki Irabu | Orel Hershiser | Mariano Rivera | 454 | 396 | 58 |
| 1999-07-15 | vs ATL | 87 | L 2-6 | 49-38 | 1 | 49,087 | Roger Clemens | Tom Glavine | Tom Glavine | Roger Clemens | | 456 | 402 | 54 |
| 1999-07-16 | vs ATL | 88 | L 7-10 | 50-38 | 1 | 50,469 | Orlando Hernandez | Greg Maddux | Russ Springer | Mariano Rivera | John Rocker | 463 | 412 | 51 |
| 1999-07-17 | vs ATL | 89 | W 11-4 | 50-39 | 1 | 55,785 | Andy Pettitte | Odalis Perez | Andy Pettitte | Odalis Perez | Jason Grimsley | 474 | 416 | 58 |
| 1999-07-18 | vs MON | 90 | W 6-0 | 51-39 | 1 | 41,930 | David Cone | Javier Vazquez | David Cone | Javier Vazquez | | 480 | 416 | 64 |
| 1999-07-19 | vs MON | 91 | L 4-6 | 51-40 | 2 | 23,404 | Hideki Irabu | Jeremy Powell | Steve Kline | Ramiro Mendoza | Ugueth Urbina | 484 | 422 | 62 |
| 1999-07-20 | vs MON | 92 | W 7-4 | 52-40 | 1 | 28,801 | Roger Clemens | Mike Thurman | Roger Clemens | Mike Thurman | Mariano Rivera | 491 | 426 | 65 |
| 1999-07-21 | vs TBA | 93 | W 4-3 | 53-40 | 1 | 27,566 | Orlando Hernandez | Bobby Witt | Orlando Hernandez | Bobby Witt | Mariano Rivera | 495 | 429 | 66 |
| 1999-07-22 | vs TBA | 94 | W 5-4 | 54-40 | 1 | 40,557 | Andy Pettitte | Rick White | Andy Pettitte | Bryan Rekar | Mariano Rivera | 500 | 433 | 67 |
| 1999-07-23 | vs CLE | 95 | W 9-8 | 55-40 | 1 | 52,704 | David Cone | Tom Candiotti | Jason Grimsley | Michael Jackson | | 509 | 441 | 68 |
| 1999-07-24 | vs CLE | 96 | W 21-1 | 56-40 | 1 | 54,870 | Hideki Irabu | Mark Langston | Hideki Irabu | Mark Langston | | 530 | 442 | 88 |
| 1999-07-25 | vs CLE | 97 | W 2-1 | 57-40 | 1 | 54,944 | Roger Clemens | Bartolo Colon | Ramiro Mendoza | Ricardo Rincon | | 532 | 443 | 89 |
| 1999-07-27 | @ CHA | 98 | W 5-3 | 58-40 | 1 | 21,364 | Orlando Hernandez | James Baldwin | Orlando Hernandez | James Baldwin | Mariano Rivera | 537 | 446 | 91 |
| 1999-07-28 | @ CHA | 99 | L 3-11 | 59-40 | 1 | 22,523 | Andy Pettitte | Jim Parque | Carlos Castillo | Andy Pettitte | | 540 | 457 | 83 |
| 1999-07-29 | @ CHA | 100 | L 1-5 | 59-41 | 1 | 24,056 | David Cone | John Snyder | John Snyder | David Cone | Keith Foulke | 541 | 462 | 79 |
| 1999-07-30 | @ BOS | 101 | W 13-3 | 59-42 | 1 | 33,777 | Hideki Irabu | Mark Portugal | Hideki Irabu | Mark Portugal | | 554 | 465 | 89 |
| 1999-07-31 | @ BOS | 102 | L 5-6 | 59-43 | 1 | 33,179 | Roger Clemens | Brian Rose | Derek Lowe | Ramiro Mendoza | | 559 | 471 | 88 |
| 1999-08-01 | @ BOS | 103 | L 4-5 | 59-44 | 2 | 33,553 | Orlando Hernandez | Bret Saberhagen | Bret Saberhagen | Orlando Hernandez | Tim Wakefield | 563 | 476 | 87 |
| 1999-08-02 | vs TOR | 104 | W 3-1 | 60-44 | 1 | 40,825 | Andy Pettitte | David Wells | Andy Pettitte | David Wells | Mariano Rivera | 566 | 477 | 89 |
| 1999-08-03 | vs TOR | 105 | L 1-3 | 60-45 | 2 | 43,110 | David Cone | Joey Hamilton | Joey Hamilton | David Cone | Billy Koch | 567 | 480 | 87 |
| 1999-08-04 | vs TOR | 106 | W 8-3 | 61-45 | 1 | 52,833 | Hideki Irabu | Kelvim Escobar | Hideki Irabu | Kelvim Escobar | | 575 | 483 | 92 |
| 1999-08-05 | @ SEA | 107 | W 7-4 | 62-45 | 1 | 45,190 | Roger Clemens | Jamie Moyer | Roger Clemens | Jamie Moyer | Mariano Rivera | 582 | 487 | 95 |
| 1999-08-06 | @ SEA | 108 | W 11-8 | 62-46 | 2 | 45,262 | Orlando Hernandez | Jeff Fassero | Allen Watson | Jeff Fassero | Mariano Rivera | 593 | 495 | 98 |
| 1999-08-07 | @ SEA | 109 | W 1-0 | 63-46 | 1 | 45,202 | Andy Pettitte | Freddy Garcia | Andy Pettitte | Freddy Garcia | Mariano Rivera | 594 | 495 | 99 |
| 1999-08-08 | @ SEA | 110 | W 9-3 | 64-46 | 1 | 45,195 | David Cone | John Halama | David Cone | John Halama | | 603 | 498 | 105 |
| 1999-08-09 | @ OAK | 111 | W 12-8 | 64-47 | 1 | 24,896 | Hideki Irabu | Jimmy Haynes | Ramiro Mendoza | Jimmy Haynes | | 615 | 506 | 109 |
| 1999-08-10 | @ OAK | 112 | L 1-6 | 64-48 | 1 | 32,474 | Roger Clemens | Omar Olivares | Omar Olivares | Roger Clemens | Doug Jones | 616 | 512 | 104 |
| 1999-08-11 | @ OAK | 113 | W 5-3 | 65-48 | 1 | 43,683 | Orlando Hernandez | Gil Heredia | Allen Watson | Doug Jones | Mariano Rivera | 621 | 515 | 106 |
| 1999-08-13 | vs MIN | 114 | W 14-2 | 65-49 | 1 | 44,568 | Andy Pettitte | LaTroy Hawkins | Andy Pettitte | LaTroy Hawkins | | 635 | 517 | 118 |
| 1999-08-14 | vs MIN | 115 | L 3-6 | 65-50 | 1 | 55,179 | David Cone | Dan Perkins | Bob Wells | David Cone | Mike Trombley | 638 | 523 | 115 |
| 1999-08-15 | vs MIN | 116 | L 3-5 | 65-51 | 1 | 56,180 | Hideki Irabu | Brad Radke | Brad Radke | Hideki Irabu | Mike Trombley | 641 | 528 | 113 |
| 1999-08-16 | vs MIN | 117 | W 2-0 | 66-51 | 1 | 36,503 | Roger Clemens | Eric Milton | Roger Clemens | Eric Milton | Mariano Rivera | 643 | 528 | 115 |
| 1999-08-17 | vs KCA | 118 | W 5-2 | 67-51 | 1 | 31,631 | Orlando Hernandez | Jose Rosado | Orlando Hernandez | Jose Rosado | Mariano Rivera | 648 | 530 | 118 |
| 1999-08-18 | vs KCA | 119 | L 0-3 | 67-52 | 1 | 38,947 | Andy Pettitte | Dan Reichert | Dan Reichert | Andy Pettitte | Jeff Montgomery | 648 | 533 | 115 |
| 1999-08-19 | vs KCA | 120 | L 1-4 | 67-53 | 1 | 42,325 | David Cone | Blake Stein | Brad Rigby | Jason Grimsley | Jeff Montgomery | 649 | 537 | 112 |
| 1999-08-20 | @ MIN | 121 | W 9-3 | 68-53 | 1 | 23,595 | Hideki Irabu | Brad Radke | Hideki Irabu | Brad Radke | Jeff Nelson | 658 | 540 | 118 |
| 1999-08-21 | @ MIN | 122 | L 1-6 | 68-54 | 1 | 32,170 | Roger Clemens | Eric Milton | Eric Milton | Roger Clemens | Eddie Guardado | 659 | 546 | 113 |
| 1999-08-22 | @ MIN | 123 | W 5-3 | 69-54 | 1 | 26,150 | Orlando Hernandez | Joe Mays | Orlando Hernandez | Joe Mays | Mariano Rivera | 664 | 549 | 115 |
| 1999-08-23 | @ TEX | 124 | W 21-3 | 69-55 | 1 | 38,024 | Andy Pettitte | John Burkett | Andy Pettitte | John Burkett | | 685 | 552 | 133 |
| 1999-08-24 | @ TEX | 125 | W 10-7 | 69-56 | 1 | 39,727 | David Cone | Mike Morgan | Ramiro Mendoza | Corey Lee | Mariano Rivera | 695 | 559 | 136 |
| 1999-08-25 | @ TEX | 126 | L 3-7 | 69-57 | 2 | 38,345 | Hideki Irabu | Esteban Loaiza | Esteban Loaiza | Hideki Irabu | | 698 | 566 | 132 |
| 1999-08-27 | vs SEA | 127 | W 8-0 | 70-57 | 1 | 51,985 | Roger Clemens | Gil Meche | Roger Clemens | Gil Meche | | 706 | 566 | 140 |
| 1999-08-28 | vs SEA | 128 | W 2-1 | 71-57 | 1 | 54,787 | Orlando Hernandez | Jamie Moyer | Mariano Rivera | Jose Paniagua | | 708 | 567 | 141 |
| 1999-08-29 | vs SEA | 129 | W 11-5 | 71-58 | 1 | 52,493 | Andy Pettitte | Paul Abbott | Andy Pettitte | Paul Abbott | Mariano Rivera | 719 | 572 | 147 |
| 1999-08-30 | vs OAK | 130 | W 7-4 | 72-58 | 1 | 32,712 | Hideki Irabu | Tim Hudson | Jeff Nelson | T.J. Mathews | Mariano Rivera | 726 | 576 | 150 |
| 1999-08-31 | vs OAK | 131 | L 2-3 | 72-59 | 1 | 33,746 | David Cone | Jimmy Haynes | Doug Jones | Ramiro Mendoza | Jason Isringhausen | 728 | 579 | 149 |
| 1999-09-01 | vs OAK | 132 | L 1-7 | 72-60 | 3 | 34,468 | Roger Clemens | Omar Olivares | Omar Olivares | Roger Clemens | | 729 | 586 | 143 |
| 1999-09-02 | vs OAK | 133 | W 9-3 | 73-60 | 2 | 33,147 | Orlando Hernandez | Gil Heredia | Orlando Hernandez | Gil Heredia | | 738 | 589 | 149 |
| 1999-09-03 | @ ANA | 134 | L 2-8 | 73-61 | 2 | 35,782 | Andy Pettitte | Tim Belcher | Tim Belcher | Andy Pettitte | | 740 | 597 | 143 |
| 1999-09-04 | @ ANA | 135 | W 9-6 | 74-61 | 2 | 30,589 | Hideki Irabu | Ramon Ortiz | Allen Watson | Juan Alvarez | Mariano Rivera | 749 | 603 | 146 |
| 1999-09-05 | @ ANA | 136 | W 8-3 | 75-61 | 2 | 35,481 | Ed Yarnall | Mike Fyhrie | Ed Yarnall | Mike Fyhrie | | 757 | 606 | 151 |
| 1999-09-06 | @ ANA | 137 | L 3-5 | 75-62 | 3 | 31,749 | Roger Clemens | Jarrod Washburn | Jarrod Washburn | Roger Clemens | Troy Percival | 760 | 611 | 149 |
| 1999-09-07 | @ KCA | 138 | L 3-6 | 75-63 | 3 | 14,207 | David Cone | Jose Rosado | Jose Rosado | David Cone | Jeff Montgomery | 763 | 617 | 146 |
| 1999-09-08 | @ KCA | 139 | W 9-5 | 76-63 | 2 | 15,247 | Orlando Hernandez | Mac Suzuki | Orlando Hernandez | Glendon Rusch | Mariano Rivera | 772 | 622 | 150 |
| 1999-09-10 | vs BOS | 140 | L 1-3 | 76-64 | 2 | 55,239 | Andy Pettitte | Pedro Martinez | Pedro Martinez | Andy Pettitte | | 773 | 625 | 148 |
| 1999-09-11 | vs BOS | 141 | L 10-11 | 76-65 | 3 | 55,422 | Hideki Irabu | Mark Portugal | Rich Garces | Hideki Irabu | Rod Beck | 783 | 636 | 147 |
| 1999-09-12 | vs BOS | 142 | L 1-4 | 76-66 | 3 | 56,028 | Roger Clemens | Bret Saberhagen | Rheal Cormier | Roger Clemens | Rod Beck | 784 | 640 | 144 |
| 1999-09-13 | @ TOR | 143 | L 1-2 | 76-67 | 3 | 30,118 | Orlando Hernandez | David Wells | David Wells | Orlando Hernandez | | 785 | 642 | 143 |
| 1999-09-14 | @ TOR | 144 | W 10-6 | 76-68 | 3 | 29,140 | David Cone | Roy Halladay | Ramiro Mendoza | Billy Koch | | 795 | 648 | 147 |
| 1999-09-15 | @ TOR | 145 | W 6-4 | 77-68 | 3 | 29,460 | Andy Pettitte | Pat Hentgen | Andy Pettitte | Pat Hentgen | Mariano Rivera | 801 | 652 | 149 |
| 1999-09-16 | @ CLE | 146 | W 9-5 | 78-68 | 3 | 43,054 | Hideki Irabu | Dave Burba | Hideki Irabu | Dave Burba | | 810 | 657 | 153 |
| 1999-09-17 | @ CLE | 147 | W 9-4 | 79-68 | 3 | 43,029 | Roger Clemens | Jaret Wright | Roger Clemens | Jaret Wright | | 819 | 661 | 158 |
| 1999-09-18 | @ CLE | 148 | L 4-5 | 79-69 | 3 | 43,002 | Orlando Hernandez | Charles Nagy | Charles Nagy | Orlando Hernandez | Michael Jackson | 823 | 666 | 157 |
| 1999-09-19 | @ CLE | 149 | W 11-7 | 79-70 | 3 | 42,969 | David Cone | Jim Brower | Allen Watson | Tom Martin | | 834 | 673 | 161 |
| 1999-09-21 | vs CHA | 150 | W 3-1 | 80-70 | 3 | 29,248 | Andy Pettitte | James Baldwin | Andy Pettitte | James Baldwin | Mariano Rivera | 837 | 674 | 163 |
| 1999-09-22 | vs CHA | 151 | W 5-4 | 81-70 | 2 | 27,549 | Hideki Irabu | Kip Wells | Mariano Rivera | Jaime Navarro | | 842 | 678 | 164 |
| 1999-09-23 | vs CHA | 152 | W 5-2 | 82-70 | 2 | 33,586 | Roger Clemens | Jim Parque | Roger Clemens | Jim Parque | Mariano Rivera | 847 | 680 | 167 |
| 1999-09-24 | vs TBA | 153 | W 4-3 | 83-70 | 2 | 44,932 | Orlando Hernandez | Bobby Witt | Mike Stanton | Norm Charlton | | 851 | 683 | 168 |
| 1999-09-25 | vs TBA | 154 | L 1-2 | 83-71 | 2 | 50,403 | David Cone | Rolando Arrojo | Rolando Arrojo | David Cone | Roberto Hernandez | 852 | 685 | 167 |
| 1999-09-26 | vs TBA | 155 | L 5-6 | 83-72 | 3 | 49,458 | Andy Pettitte | Wilson Alvarez | Cory Lidle | Ramiro Mendoza | Roberto Hernandez | 857 | 691 | 166 |
| 1999-09-27 | vs TBA | 156 | L 6-10 | 84-72 | 2 | 41,355 | Hideki Irabu | Dave Eiland | Mike Duvall | Hideki Irabu | Jeff Sparks | 863 | 701 | 162 |
| 1999-09-28 | @ BAL | 157 | W 9-5 | 85-72 | 2 | 44,711 | Ed Yarnall | Sidney Ponson | Ramiro Mendoza | Sidney Ponson | | 872 | 706 | 166 |
| 1999-09-30 | @ BAL | 158 | L 0-5 | 85-74 | 4 | 44,568 | Roger Clemens | Mike Mussina | Mike Mussina | Roger Clemens | | 872 | 711 | 161 |
| 1999-09-30 | @ BAL | 159 | W 12-5 | 85-74 | 4 | 47,446 | Orlando Hernandez | Matt Riley | Orlando Hernandez | Jim Corsi | | 884 | 716 | 168 |
| 1999-10-01 | @ TBA | 160 | W 11-7 | 85-75 | 3 | 27,248 | Andy Pettitte | Rolando Arrojo | Ramiro Mendoza | Rolando Arrojo | Mariano Rivera | 895 | 723 | 172 |
| 1999-10-02 | @ TBA | 161 | W 3-2 | 86-75 | 3 | 40,756 | David Cone | Wilson Alvarez | David Cone | Wilson Alvarez | Mariano Rivera | 898 | 725 | 173 |
| 1999-10-03 | @ TBA | 162 | L 2-6 | 86-76 | 3 | 31,292 | Jeff Juden | Cory Lidle | Eddie Gaillard | Jeff Juden | Roberto Hernandez | 900 | 731 | 169 |