| 1999-04-06 | @ ANA | 1 | L 5-6 | 0-1 | 3 | 39,936 | Jaret Wright | Tim Belcher | Mike Holtz | Steve Karsay | Troy Percival | 5 | 6 | -1 |
| 1999-04-07 | @ ANA | 2 | W 9-1 | 1-1 | 1 | 21,689 | Dave Burba | Ken Hill | Dave Burba | Ken Hill | | 14 | 7 | 7 |
| 1999-04-08 | @ ANA | 3 | W 9-1 | 2-1 | 1 | 25,084 | Bartolo Colon | Steve Sparks | Bartolo Colon | Steve Sparks | | 23 | 8 | 15 |
| 1999-04-09 | @ MIN | 4 | W 14-5 | 2-2 | 2 | 16,348 | Charles Nagy | LaTroy Hawkins | Charles Nagy | LaTroy Hawkins | | 37 | 13 | 24 |
| 1999-04-10 | @ MIN | 5 | W 12-7 | 2-3 | 3 | 18,829 | Dwight Gooden | Benj Sampson | Steve Karsay | Mike Lincoln | | 49 | 20 | 29 |
| 1999-04-11 | @ MIN | 6 | W 9-8 | 3-3 | 1 | 12,430 | Jaret Wright | Brad Radke | Jaret Wright | Brad Radke | Michael Jackson | 58 | 28 | 30 |
| 1999-04-12 | vs KCA | 7 | W 5-2 | 4-3 | 1 | 42,798 | Dave Burba | Jose Rosado | Paul Shuey | Jose Santiago | | 63 | 30 | 33 |
| 1999-04-14 | vs KCA | 8 | W 11-4 | 4-4 | 1 | 42,926 | Bartolo Colon | Jeff Suppan | Bartolo Colon | Jeff Suppan | | 74 | 34 | 40 |
| 1999-04-17 | vs MIN | 9 | W 5-1 | 5-4 | 2 | 40,582 | Charles Nagy | Brad Radke | Charles Nagy | Brad Radke | | 79 | 35 | 44 |
| 1999-04-17 | vs MIN | 10 | L 8-13 | 5-4 | 2 | 42,860 | Jaret Wright | Eric Milton | Rick Aguilera | Michael Jackson | | 87 | 48 | 39 |
| 1999-04-18 | vs MIN | 11 | W 3-2 | 7-4 | 1 | 42,317 | Dave Burba | Mike Lincoln | Paul Shuey | Bob Wells | Michael Jackson | 90 | 50 | 40 |
| 1999-04-20 | vs OAK | 12 | W 5-1 | 8-4 | 1 | 42,954 | Bartolo Colon | Kenny Rogers | Bartolo Colon | Kenny Rogers | | 95 | 51 | 44 |
| 1999-04-21 | vs OAK | 13 | W 5-4 | 9-4 | 1 | 41,933 | Dwight Gooden | Gil Heredia | Steve Reed | Billy Taylor | | 100 | 55 | 45 |
| 1999-04-22 | vs OAK | 14 | L 1-4 | 9-5 | 1 | 42,937 | Charles Nagy | Tom Candiotti | Tom Candiotti | Charles Nagy | Billy Taylor | 101 | 59 | 42 |
| 1999-04-23 | @ BOS | 15 | W 7-6 | 10-5 | 1 | 29,921 | Jaret Wright | Pat Rapp | Steve Karsay | Jim Corsi | Michael Jackson | 108 | 65 | 43 |
| 1999-04-24 | @ BOS | 16 | L 4-9 | 10-6 | 1 | 29,481 | Dave Burba | Bret Saberhagen | Tim Harikkala | Rich DeLucia | | 112 | 74 | 38 |
| 1999-04-25 | @ BOS | 17 | L 2-3 | 10-7 | 1 | 30,472 | Bartolo Colon | Pedro Martinez | Pedro Martinez | Paul Shuey | | 114 | 77 | 37 |
| 1999-04-26 | @ OAK | 18 | W 5-4 | 11-7 | 1 | 7,646 | Dwight Gooden | Gil Heredia | Steve Karsay | Billy Taylor | Michael Jackson | 119 | 81 | 38 |
| 1999-04-27 | @ OAK | 19 | W 8-5 | 12-7 | 1 | 7,161 | Charles Nagy | Tom Candiotti | Charles Nagy | Tom Candiotti | Michael Jackson | 127 | 86 | 41 |
| 1999-04-28 | @ OAK | 20 | W 4-1 | 13-7 | 1 | 9,555 | Jaret Wright | Jimmy Haynes | Jaret Wright | Jimmy Haynes | Michael Jackson | 131 | 87 | 44 |
| 1999-04-29 | @ OAK | 21 | W 8-3 | 14-7 | 1 | 10,115 | Dave Burba | Mike Oquist | Dave Burba | Mike Oquist | | 139 | 90 | 49 |
| 1999-04-30 | @ TEX | 22 | L 5-7 | 14-8 | 1 | 36,556 | Bartolo Colon | Rick Helling | Rick Helling | Bartolo Colon | John Wetteland | 144 | 97 | 47 |
| 1999-05-01 | @ TEX | 23 | W 5-3 | 15-8 | 1 | 45,579 | Dwight Gooden | Aaron Sele | Dwight Gooden | Aaron Sele | Michael Jackson | 149 | 100 | 49 |
| 1999-05-02 | @ TEX | 24 | L 6-8 | 15-9 | 1 | 29,921 | Charles Nagy | Mark Clark | Mark Clark | Charles Nagy | John Wetteland | 155 | 108 | 47 |
| 1999-05-03 | @ TEX | 25 | W 10-4 | 15-10 | 2 | 31,181 | Jaret Wright | Mike Morgan | Jaret Wright | Mike Morgan | | 165 | 112 | 53 |
| 1999-05-05 | vs SEA | 26 | L 5-6 | 15-11 | 2 | 42,991 | Dave Burba | Jeff Fassero | Jeff Fassero | Dave Burba | Jose Mesa | 170 | 118 | 52 |
| 1999-05-06 | vs SEA | 27 | W 8-4 | 16-11 | 2 | 41,962 | Bartolo Colon | Jamie Moyer | Bartolo Colon | Eric Weaver | | 178 | 122 | 56 |
| 1999-05-07 | vs TBA | 28 | W 20-11 | 17-11 | 1 | 40,601 | Dwight Gooden | Bobby Witt | Paul Wagner | Jim Mecir | | 198 | 133 | 65 |
| 1999-05-08 | vs TBA | 29 | L 6-7 | 17-12 | 2 | 40,590 | Charles Nagy | Esteban Yan | Bryan Rekar | Charles Nagy | Roberto Hernandez | 204 | 140 | 64 |
| 1999-05-09 | vs TBA | 30 | W 5-4 | 18-12 | 1 | 42,835 | Jaret Wright | Wilson Alvarez | Jaret Wright | Wilson Alvarez | Michael Jackson | 209 | 144 | 65 |
| 1999-05-10 | vs BAL | 31 | W 6-4 | 19-12 | 1 | 40,615 | Dave Burba | Juan Guzman | Dave Burba | Juan Guzman | Michael Jackson | 215 | 148 | 67 |
| 1999-05-11 | vs BAL | 32 | W 11-6 | 19-13 | 1 | 40,587 | Bartolo Colon | Sidney Ponson | Bartolo Colon | Sidney Ponson | | 226 | 154 | 72 |
| 1999-05-12 | vs BAL | 33 | W 6-5 | 20-13 | 1 | 42,939 | Dwight Gooden | Mike Mussina | Paul Assenmacher | Mike Timlin | Paul Shuey | 232 | 159 | 73 |
| 1999-05-14 | @ DET | 34 | W 4-2 | 21-13 | 1 | 21,844 | Charles Nagy | Brian Moehler | Steve Karsay | Doug Brocail | Paul Shuey | 236 | 161 | 75 |
| 1999-05-15 | @ DET | 35 | W 12-7 | 21-14 | 1 | 39,769 | Dave Burba | Dave Mlicki | Dave Burba | Dave Mlicki | | 248 | 168 | 80 |
| 1999-05-16 | @ DET | 36 | L 3-9 | 21-15 | 1 | 29,731 | Jaret Wright | Jeff Weaver | Jeff Weaver | Jaret Wright | Masao Kida | 251 | 177 | 74 |
| 1999-05-17 | @ CHA | 37 | W 13-9 | 21-16 | 1 | 17,101 | Bartolo Colon | Jaime Navarro | Bartolo Colon | Jaime Navarro | | 264 | 186 | 78 |
| 1999-05-18 | @ CHA | 38 | W 13-0 | 22-16 | 1 | 13,429 | Dwight Gooden | James Baldwin | Dwight Gooden | James Baldwin | | 277 | 186 | 91 |
| 1999-05-19 | @ CHA | 39 | W 13-7 | 22-17 | 1 | 14,854 | Charles Nagy | Jim Parque | Charles Nagy | Jim Parque | | 290 | 193 | 97 |
| 1999-05-21 | vs DET | 40 | L 6-9 | 22-18 | 2 | 43,290 | Dave Burba | Willie Blair | C.J. Nitkowski | Paul Shuey | Todd Jones | 296 | 202 | 94 |
| 1999-05-22 | vs DET | 41 | L 2-6 | 22-19 | 3 | 40,991 | Jaret Wright | Jeff Weaver | Jeff Weaver | Jaret Wright | | 298 | 208 | 90 |
| 1999-05-23 | vs DET | 42 | W 7-4 | 23-19 | 2 | 40,874 | Bartolo Colon | Justin Thompson | Paul Shuey | Todd Jones | | 305 | 212 | 93 |
| 1999-05-24 | vs CHA | 43 | L 3-10 | 24-19 | 2 | 43,208 | Dwight Gooden | James Baldwin | Sean Lowe | Dwight Gooden | | 308 | 222 | 86 |
| 1999-05-25 | vs CHA | 44 | W 3-1 | 25-19 | 1 | 42,161 | Charles Nagy | Jim Parque | Charles Nagy | Jim Parque | Michael Jackson | 311 | 223 | 88 |
| 1999-05-26 | vs CHA | 45 | W 6-2 | 26-19 | 1 | 43,228 | Dave Burba | Mike Sirotka | Dave Burba | Mike Sirotka | Paul Shuey | 317 | 225 | 92 |
| 1999-05-28 | vs BOS | 46 | L 5-12 | 27-19 | 1 | 43,287 | Jaret Wright | Tim Wakefield | Tim Wakefield | Jaret Wright | Derek Lowe | 322 | 237 | 85 |
| 1999-05-29 | vs BOS | 47 | L 2-4 | 27-20 | 1 | 43,255 | Bartolo Colon | Pedro Martinez | Pedro Martinez | Bartolo Colon | Tom Gordon | 324 | 241 | 83 |
| 1999-05-30 | vs BOS | 48 | L 2-4 | 27-21 | 1 | 43,207 | Dwight Gooden | Brian Rose | Brian Rose | Dwight Gooden | Tom Gordon | 326 | 245 | 81 |
| 1999-05-31 | @ NYA | 49 | W 7-1 | 28-21 | 1 | 46,605 | Charles Nagy | Orlando Hernandez | Charles Nagy | Orlando Hernandez | | 333 | 246 | 87 |
| 1999-06-01 | @ NYA | 50 | L 5-11 | 29-21 | 1 | 32,759 | Dave Burba | Roger Clemens | Roger Clemens | Dave Burba | | 338 | 257 | 81 |
| 1999-06-02 | @ NYA | 51 | W 10-7 | 29-22 | 1 | 36,955 | Jaret Wright | Andy Pettitte | Steve Karsay | Andy Pettitte | Michael Jackson | 348 | 264 | 84 |
| 1999-06-04 | vs CHN | 52 | L 4-5 | 29-23 | 1 | 43,011 | Bartolo Colon | Terry Mulholland | Rick Aguilera | Michael Jackson | Terry Adams | 352 | 269 | 83 |
| 1999-06-05 | vs CHN | 53 | W 8-7 | 30-23 | 1 | 43,085 | Dwight Gooden | Jon Lieber | Michael Jackson | Scott Sanders | | 360 | 276 | 84 |
| 1999-06-06 | vs CHN | 54 | W 4-2 | 31-23 | 1 | 43,010 | Charles Nagy | Steve Trachsel | Charles Nagy | Steve Trachsel | Paul Shuey | 364 | 278 | 86 |
| 1999-06-08 | vs MIL | 55 | L 1-2 | 31-24 | 1 | 42,300 | Dave Burba | Steve Woodard | Rafael Roque | Paul Assenmacher | Bob Wickman | 365 | 280 | 85 |
| 1999-06-09 | vs MIL | 56 | W 6-5 | 32-24 | 1 | 43,160 | Jaret Wright | Jim Abbott | Michael Jackson | Rafael Roque | | 371 | 285 | 86 |
| 1999-06-10 | vs MIL | 57 | L 9-15 | 33-24 | 1 | 43,196 | Bartolo Colon | Hideo Nomo | Hideo Nomo | Bartolo Colon | | 380 | 300 | 80 |
| 1999-06-11 | @ CIN | 58 | W 8-6 | 34-24 | 1 | 42,928 | Dwight Gooden | Steve Parris | Paul Shuey | Scott Williamson | Michael Jackson | 388 | 306 | 82 |
| 1999-06-12 | @ CIN | 59 | W 4-3 | 35-24 | 1 | 52,804 | Charles Nagy | Pete Harnisch | Charles Nagy | Pete Harnisch | Michael Jackson | 392 | 309 | 83 |
| 1999-06-13 | @ CIN | 60 | W 7-3 | 36-24 | 1 | 45,593 | Dave Burba | Steve Avery | Dave Burba | Steve Avery | Steve Karsay | 399 | 312 | 87 |
| 1999-06-15 | vs OAK | 61 | W 8-3 | 37-24 | 1 | 43,231 | Jaret Wright | Jimmy Haynes | Jaret Wright | Jimmy Haynes | | 407 | 315 | 92 |
| 1999-06-16 | vs OAK | 62 | W 9-8 | 38-24 | 1 | 43,163 | Bartolo Colon | Gil Heredia | Steve Karsay | Billy Taylor | | 416 | 323 | 93 |
| 1999-06-17 | vs OAK | 63 | W 10-6 | 38-25 | 1 | 43,262 | Dwight Gooden | Kenny Rogers | Paul Shuey | Tim Worrell | | 426 | 329 | 97 |
| 1999-06-18 | vs SEA | 64 | L 4-9 | 38-26 | 1 | 43,126 | Charles Nagy | John Halama | John Halama | Charles Nagy | | 430 | 338 | 92 |
| 1999-06-19 | vs SEA | 65 | W 10-6 | 38-27 | 1 | 43,205 | Dave Burba | Melvin Bunch | Dave Burba | Allen Watson | Michael Jackson | 440 | 344 | 96 |
| 1999-06-20 | vs SEA | 66 | W 13-5 | 38-28 | 1 | 43,070 | Jaret Wright | Frankie Rodriguez | Jaret Wright | Frankie Rodriguez | | 453 | 349 | 104 |
| 1999-06-21 | vs SEA | 67 | W 4-3 | 39-28 | 1 | 43,093 | Bartolo Colon | Jamie Moyer | Steve Karsay | Jose Mesa | | 457 | 352 | 105 |
| 1999-06-22 | @ TOR | 68 | L 3-4 | 39-29 | 1 | 22,197 | Dwight Gooden | Kelvim Escobar | Kelvim Escobar | Dwight Gooden | Billy Koch | 460 | 356 | 104 |
| 1999-06-23 | @ TOR | 69 | W 9-6 | 40-29 | 1 | 23,271 | Charles Nagy | Pat Hentgen | Charles Nagy | Paul Quantrill | | 469 | 362 | 107 |
| 1999-06-24 | @ TOR | 70 | L 0-3 | 40-30 | 1 | 26,117 | Dave Burba | Roy Halladay | Roy Halladay | Dave Burba | Billy Koch | 469 | 365 | 104 |
| 1999-06-25 | @ KCA | 71 | L 2-8 | 40-31 | 1 | 32,147 | Jaret Wright | Jeff Suppan | Jeff Suppan | Jaret Wright | | 471 | 373 | 98 |
| 1999-06-26 | @ KCA | 72 | L 7-11 | 41-31 | 1 | 29,358 | Bartolo Colon | Chris Fussell | Jeff Montgomery | Ricardo Rincon | | 478 | 384 | 94 |
| 1999-06-27 | @ KCA | 73 | W 6-5 | 42-31 | 1 | 17,094 | Dwight Gooden | Jose Rosado | Steve Reed | Tim Byrdak | Michael Jackson | 484 | 389 | 95 |
| 1999-06-28 | @ KCA | 74 | W 6-1 | 43-31 | 1 | 23,429 | Charles Nagy | Jay Witasick | Charles Nagy | Jay Witasick | | 490 | 390 | 100 |
| 1999-06-29 | vs MIN | 75 | W 5-4 | 44-31 | 1 | 43,159 | Dave Burba | Brad Radke | Steve Reed | Mike Trombley | | 495 | 394 | 101 |
| 1999-06-30 | vs MIN | 76 | L 3-5 | 44-32 | 1 | 43,061 | Jaret Wright | Eric Milton | Eric Milton | Jaret Wright | Mike Trombley | 498 | 399 | 99 |
| 1999-07-01 | vs MIN | 77 | W 7-5 | 45-32 | 1 | 43,010 | Bartolo Colon | Joe Mays | Bartolo Colon | Hector Carrasco | Michael Jackson | 505 | 404 | 101 |
| 1999-07-02 | vs KCA | 78 | L 7-9 | 45-33 | 1 | 43,172 | Dwight Gooden | Jose Rosado | Matt Whisenant | Paul Shuey | | 512 | 413 | 99 |
| 1999-07-03 | vs KCA | 79 | W 9-8 | 46-33 | 2 | 43,086 | Charles Nagy | Jay Witasick | Tom Candiotti | Marc Pisciotta | Michael Jackson | 521 | 421 | 100 |
| 1999-07-03 | vs KCA | 80 | W 9-5 | 46-33 | 2 | 40,707 | Mark Langston | Don Wengert | Mark Langston | Don Wengert | Michael Jackson | 530 | 426 | 104 |
| 1999-07-04 | vs KCA | 81 | L 9-10 | 48-33 | 1 | 43,018 | Dave Burba | Kevin Appier | Kevin Appier | Dave Burba | Tim Byrdak | 539 | 436 | 103 |
| 1999-07-06 | @ MIN | 82 | W 3-1 | 49-33 | 1 | 12,579 | Jaret Wright | Eric Milton | Jaret Wright | Eric Milton | Michael Jackson | 542 | 437 | 105 |
| 1999-07-07 | @ MIN | 83 | L 3-4 | 49-34 | 1 | 12,710 | Bartolo Colon | Joe Mays | Mike Trombley | Steve Reed | | 545 | 441 | 104 |
| 1999-07-08 | @ MIN | 84 | W 9-2 | 50-34 | 1 | 14,118 | Charles Nagy | Mike Lincoln | Charles Nagy | Mike Lincoln | | 554 | 443 | 111 |
| 1999-07-09 | vs CIN | 85 | L 2-3 | 50-35 | 1 | 43,208 | Dave Burba | Steve Avery | Steve Avery | Dave Burba | Scott Williamson | 556 | 446 | 110 |
| 1999-07-10 | vs CIN | 86 | W 11-10 | 51-35 | 1 | 43,127 | Tom Candiotti | Ron Villone | Michael Jackson | Scott Williamson | | 567 | 456 | 111 |
| 1999-07-11 | vs CIN | 87 | L 4-9 | 51-36 | 1 | 43,167 | Jaret Wright | Brett Tomko | Danny Graves | Paul Shuey | | 571 | 465 | 106 |
| 1999-07-15 | @ PIT | 88 | W 2-0 | 52-36 | 1 | 39,620 | Bartolo Colon | Jason Schmidt | Bartolo Colon | Jason Schmidt | Michael Jackson | 573 | 465 | 108 |
| 1999-07-16 | @ PIT | 89 | L 3-11 | 53-36 | 1 | 43,519 | Dave Burba | Francisco Cordova | Francisco Cordova | Dave Burba | | 576 | 476 | 100 |
| 1999-07-17 | @ PIT | 90 | L 10-13 | 53-37 | 1 | 43,299 | Charles Nagy | Kris Benson | Kris Benson | Charles Nagy | Mike Williams | 586 | 489 | 97 |
| 1999-07-18 | @ HOU | 91 | L 0-2 | 53-38 | 1 | 50,299 | Jaret Wright | Mike Hampton | Mike Hampton | Jaret Wright | | 586 | 491 | 95 |
| 1999-07-19 | @ HOU | 92 | L 2-3 | 53-39 | 1 | 34,276 | Mark Langston | Chris Holt | Jose Cabrera | Tom Candiotti | | 588 | 494 | 94 |
| 1999-07-20 | @ HOU | 93 | W 7-1 | 54-39 | 1 | 41,133 | Bartolo Colon | Shane Reynolds | Bartolo Colon | Shane Reynolds | | 595 | 495 | 100 |
| 1999-07-21 | vs TOR | 94 | L 3-4 | 54-40 | 1 | 43,218 | Dave Burba | Pat Hentgen | John Frascatore | Michael Jackson | Billy Koch | 598 | 499 | 99 |
| 1999-07-22 | vs TOR | 95 | L 3-4 | 54-41 | 1 | 43,138 | Charles Nagy | David Wells | David Wells | Charles Nagy | Billy Koch | 601 | 503 | 98 |
| 1999-07-23 | @ NYA | 96 | L 8-9 | 54-42 | 1 | 52,704 | Tom Candiotti | David Cone | Jason Grimsley | Michael Jackson | | 609 | 512 | 97 |
| 1999-07-24 | @ NYA | 97 | L 1-21 | 54-43 | 1 | 54,870 | Mark Langston | Hideki Irabu | Hideki Irabu | Mark Langston | | 610 | 533 | 77 |
| 1999-07-25 | @ NYA | 98 | L 1-2 | 54-44 | 1 | 54,944 | Bartolo Colon | Roger Clemens | Ramiro Mendoza | Ricardo Rincon | | 611 | 535 | 76 |
| 1999-07-26 | vs DET | 99 | W 6-3 | 55-44 | 1 | 43,157 | Dave Burba | Justin Thompson | Dave Burba | Justin Thompson | Michael Jackson | 617 | 538 | 79 |
| 1999-07-27 | vs DET | 100 | W 14-5 | 55-45 | 1 | 43,042 | Charles Nagy | Dave Borkowski | Charles Nagy | Dave Borkowski | | 631 | 543 | 88 |
| 1999-07-28 | vs DET | 101 | W 7-2 | 56-45 | 1 | 43,162 | Dwight Gooden | Brian Moehler | Dwight Gooden | Brian Moehler | | 638 | 545 | 93 |
| 1999-07-30 | vs CHA | 102 | W 10-2 | 56-46 | 1 | 43,181 | Bartolo Colon | Mike Sirotka | Bartolo Colon | Mike Sirotka | | 648 | 547 | 101 |
| 1999-07-31 | vs CHA | 103 | W 13-10 | 57-46 | 1 | 43,209 | Dave Burba | Jaime Navarro | Paul Shuey | Carlos Castillo | Michael Jackson | 661 | 557 | 104 |
| 1999-08-01 | vs CHA | 104 | L 3-6 | 57-47 | 1 | 43,067 | Charles Nagy | James Baldwin | James Baldwin | Charles Nagy | Bob Howry | 664 | 563 | 101 |
| 1999-08-02 | @ BOS | 105 | W 7-5 | 58-47 | 1 | 33,218 | Dwight Gooden | Pat Rapp | Steve Karsay | Rich Garces | Michael Jackson | 671 | 568 | 103 |
| 1999-08-03 | @ BOS | 106 | W 5-4 | 59-47 | 1 | 33,650 | Jaret Wright | Pedro Martinez | Paul Shuey | Tim Wakefield | Michael Jackson | 676 | 572 | 104 |
| 1999-08-04 | @ BOS | 107 | L 2-7 | 59-48 | 1 | 33,282 | Bartolo Colon | Mark Portugal | Mark Portugal | Bartolo Colon | | 678 | 579 | 99 |
| 1999-08-06 | @ TBA | 108 | L 2-4 | 59-49 | 1 | 34,623 | Dave Burba | Rolando Arrojo | Esteban Yan | Dave Burba | Roberto Hernandez | 680 | 583 | 97 |
| 1999-08-07 | @ TBA | 109 | W 15-10 | 60-49 | 1 | 39,512 | Charles Nagy | Bobby Witt | Charles Nagy | Bobby Witt | | 695 | 593 | 102 |
| 1999-08-08 | @ TBA | 110 | L 3-5 | 60-50 | 1 | 33,052 | Jaret Wright | Wilson Alvarez | Wilson Alvarez | Jaret Wright | Roberto Hernandez | 698 | 598 | 100 |
| 1999-08-09 | @ ANA | 111 | W 4-0 | 61-50 | 1 | 22,013 | Bartolo Colon | Ken Hill | Bartolo Colon | Ken Hill | | 702 | 598 | 104 |
| 1999-08-10 | @ ANA | 112 | W 2-1 | 62-50 | 1 | 25,777 | Mark Langston | Chuck Finley | Ricardo Rincon | Mark Petkovsek | Michael Jackson | 704 | 599 | 105 |
| 1999-08-11 | @ ANA | 113 | W 4-3 | 63-50 | 1 | 26,399 | Dave Burba | Steve Sparks | Dave Burba | Steve Sparks | Michael Jackson | 708 | 602 | 106 |
| 1999-08-13 | vs BAL | 114 | W 6-3 | 64-50 | 1 | 43,073 | Charles Nagy | Scott Erickson | Ricardo Rincon | Scott Erickson | Michael Jackson | 714 | 605 | 109 |
| 1999-08-14 | vs BAL | 115 | W 7-1 | 65-50 | 1 | 43,103 | Steve Karsay | Jason Johnson | Steve Karsay | Jason Johnson | | 721 | 606 | 115 |
| 1999-08-15 | vs BAL | 116 | W 5-1 | 66-50 | 1 | 43,020 | Bartolo Colon | Sidney Ponson | Bartolo Colon | Sidney Ponson | | 726 | 607 | 119 |
| 1999-08-16 | vs TEX | 117 | L 5-13 | 67-50 | 1 | 43,226 | Dave Burba | Rick Helling | Mike Munoz | Ricardo Rincon | | 731 | 620 | 111 |
| 1999-08-17 | vs TEX | 118 | L 4-15 | 68-50 | 1 | 42,987 | Mark Langston | Aaron Sele | Aaron Sele | Mark Langston | | 735 | 635 | 100 |
| 1999-08-18 | vs TEX | 119 | L 1-6 | 68-51 | 1 | 42,997 | Charles Nagy | John Burkett | John Burkett | Charles Nagy | | 736 | 641 | 95 |
| 1999-08-19 | vs TEX | 120 | W 8-0 | 69-51 | 1 | 43,263 | Steve Karsay | Mike Morgan | Steve Karsay | Mike Morgan | | 744 | 641 | 103 |
| 1999-08-20 | @ SEA | 121 | W 7-4 | 70-51 | 1 | 44,915 | Bartolo Colon | John Halama | Bartolo Colon | John Halama | Michael Jackson | 751 | 645 | 106 |
| 1999-08-21 | @ SEA | 122 | W 6-0 | 71-51 | 1 | 44,891 | Dave Burba | Gil Meche | Dave Burba | Gil Meche | | 757 | 645 | 112 |
| 1999-08-22 | @ SEA | 123 | W 7-4 | 72-51 | 1 | 44,941 | Chris Haney | Jamie Moyer | David Riske | Jose Mesa | Michael Jackson | 764 | 649 | 115 |
| 1999-08-23 | @ SEA | 124 | L 1-4 | 72-52 | 1 | 44,689 | Charles Nagy | Paul Abbott | Paul Abbott | Charles Nagy | Jose Mesa | 765 | 653 | 112 |
| 1999-08-24 | @ OAK | 125 | L 10-11 | 72-53 | 1 | 17,417 | Steve Karsay | Tim Hudson | T.J. Mathews | Paul Shuey | | 775 | 664 | 111 |
| 1999-08-25 | @ OAK | 126 | W 12-4 | 72-54 | 1 | 21,328 | Bartolo Colon | Mike Oquist | Bartolo Colon | Mike Oquist | | 787 | 668 | 119 |
| 1999-08-27 | vs TBA | 127 | W 2-1 | 73-54 | 1 | 43,303 | Dave Burba | Rolando Arrojo | Dave Burba | Rolando Arrojo | Michael Jackson | 789 | 669 | 120 |
| 1999-08-28 | vs TBA | 128 | W 3-0 | 74-54 | 1 | 43,190 | Charles Nagy | Bobby Witt | Charles Nagy | Bobby Witt | Michael Jackson | 792 | 669 | 123 |
| 1999-08-29 | vs TBA | 129 | L 4-6 | 74-55 | 1 | 43,151 | Chris Haney | Wilson Alvarez | Wilson Alvarez | Chris Haney | Roberto Hernandez | 796 | 675 | 121 |
| 1999-08-30 | vs ANA | 130 | W 7-5 | 75-55 | 1 | 43,295 | Bartolo Colon | Ramon Ortiz | Bartolo Colon | Al Levine | Michael Jackson | 803 | 680 | 123 |
| 1999-08-31 | vs ANA | 131 | W 14-12 | 76-55 | 1 | 43,284 | Dwight Gooden | Chuck Finley | Jim Poole | Troy Percival | Paul Shuey | 817 | 692 | 125 |
| 1999-09-01 | vs ANA | 132 | W 8-1 | 77-55 | 1 | 43,399 | Dave Burba | Jarrod Washburn | Dave Burba | Jarrod Washburn | | 825 | 693 | 132 |
| 1999-09-02 | vs ANA | 133 | W 6-5 | 78-55 | 1 | 43,369 | Charles Nagy | Steve Sparks | Charles Nagy | Steve Sparks | Michael Jackson | 831 | 698 | 133 |
| 1999-09-03 | @ BAL | 134 | W 7-6 | 79-55 | 1 | 41,521 | Chris Haney | Jason Johnson | Paul Assenmacher | Alberto Reyes | Michael Jackson | 838 | 704 | 134 |
| 1999-09-04 | @ BAL | 135 | L 1-3 | 79-56 | 1 | 47,095 | Bartolo Colon | Doug Linton | Doug Linton | Bartolo Colon | Mike Timlin | 839 | 707 | 132 |
| 1999-09-05 | @ BAL | 136 | W 15-7 | 79-57 | 1 | 44,214 | Dwight Gooden | Sidney Ponson | Jim Brower | Sidney Ponson | | 854 | 714 | 140 |
| 1999-09-06 | @ BAL | 137 | W 7-6 | 80-57 | 1 | 40,540 | Dave Burba | Doug Johns | Dave Burba | Doug Johns | Michael Jackson | 861 | 720 | 141 |
| 1999-09-07 | @ TEX | 138 | L 3-4 | 80-58 | 1 | 26,011 | Charles Nagy | Aaron Sele | Aaron Sele | Steve Reed | John Wetteland | 864 | 724 | 140 |
| 1999-09-08 | @ TEX | 139 | L 0-3 | 80-59 | 1 | 29,889 | Chris Haney | John Burkett | John Burkett | Chris Haney | John Wetteland | 864 | 727 | 137 |
| 1999-09-10 | @ CHA | 140 | W 14-6 | 80-60 | 1 | 19,132 | Bartolo Colon | Kip Wells | Bartolo Colon | Kip Wells | | 878 | 733 | 145 |
| 1999-09-11 | @ CHA | 141 | W 4-3 | 81-60 | 1 | 34,400 | Dave Burba | Jim Parque | Dave Burba | Jim Parque | Michael Jackson | 882 | 736 | 146 |
| 1999-09-12 | @ CHA | 142 | L 3-4 | 81-61 | 1 | 20,481 | Jaret Wright | Mike Sirotka | Mike Sirotka | Jaret Wright | Bob Howry | 885 | 740 | 145 |
| 1999-09-13 | vs BOS | 143 | W 11-7 | 81-62 | 1 | 43,264 | Charles Nagy | Tim Wakefield | Charles Nagy | Tim Wakefield | Paul Shuey | 896 | 747 | 149 |
| 1999-09-14 | vs BOS | 144 | L 3-12 | 82-62 | 1 | 43,203 | Dwight Gooden | Ramon Martinez | Derek Lowe | Dwight Gooden | | 899 | 759 | 140 |
| 1999-09-15 | vs BOS | 145 | L 4-6 | 82-63 | 1 | 43,224 | Bartolo Colon | Pedro Martinez | John Wasdin | Jim Brower | | 903 | 765 | 138 |
| 1999-09-16 | vs NYA | 146 | L 5-9 | 82-64 | 1 | 43,054 | Dave Burba | Hideki Irabu | Hideki Irabu | Dave Burba | | 908 | 774 | 134 |
| 1999-09-17 | vs NYA | 147 | L 4-9 | 82-65 | 1 | 43,029 | Jaret Wright | Roger Clemens | Roger Clemens | Jaret Wright | | 912 | 783 | 129 |
| 1999-09-18 | vs NYA | 148 | W 5-4 | 83-65 | 1 | 43,002 | Charles Nagy | Orlando Hernandez | Charles Nagy | Orlando Hernandez | Michael Jackson | 917 | 787 | 130 |
| 1999-09-19 | vs NYA | 149 | L 7-11 | 84-65 | 1 | 42,969 | Jim Brower | David Cone | Allen Watson | Tom Martin | | 924 | 798 | 126 |
| 1999-09-20 | @ DET | 150 | L 3-4 | 84-66 | 1 | 26,106 | Dwight Gooden | C.J. Nitkowski | Todd Jones | David Riske | | 927 | 802 | 125 |
| 1999-09-21 | @ DET | 151 | W 6-1 | 85-66 | 1 | 24,155 | Dave Burba | Dave Borkowski | Dave Burba | Dave Borkowski | | 933 | 803 | 130 |
| 1999-09-22 | @ DET | 152 | W 9-1 | 86-66 | 1 | 27,355 | Jaret Wright | Brian Moehler | Jaret Wright | Brian Moehler | | 942 | 804 | 138 |
| 1999-09-23 | @ DET | 153 | L 5-7 | 86-67 | 1 | 34,970 | Charles Nagy | Willie Blair | Willie Blair | Charles Nagy | Todd Jones | 947 | 811 | 136 |
| 1999-09-24 | @ TOR | 154 | W 18-4 | 86-68 | 1 | 26,620 | Jim Brower | Peter Munro | Jim Brower | Peter Munro | | 965 | 815 | 150 |
| 1999-09-25 | @ TOR | 155 | W 9-6 | 87-68 | 1 | 32,029 | Bartolo Colon | Paul Spoljaric | Bartolo Colon | Paul Spoljaric | Michael Jackson | 974 | 821 | 153 |
| 1999-09-26 | @ TOR | 156 | W 11-7 | 87-69 | 1 | 34,253 | Dave Burba | Pat Hentgen | Paul Shuey | Billy Koch | | 985 | 828 | 157 |
| 1999-09-28 | @ KCA | 157 | W 2-1 | 88-69 | 1 | 11,009 | Jaret Wright | Jay Witasick | Jim Brower | Jay Witasick | Michael Jackson | 987 | 829 | 158 |
| 1999-09-29 | @ KCA | 158 | L 2-5 | 88-70 | 1 | 11,814 | Charles Nagy | Jose Rosado | Jose Rosado | Charles Nagy | | 989 | 834 | 155 |
| 1999-09-30 | vs TOR | 159 | W 9-2 | 89-70 | 1 | 43,201 | Bartolo Colon | Paul Spoljaric | Bartolo Colon | Paul Spoljaric | | 998 | 836 | 162 |
| 1999-10-01 | vs TOR | 160 | L 6-8 | 89-71 | 1 | 43,040 | Dwight Gooden | Peter Munro | Paul Quantrill | Steve Karsay | Billy Koch | 1004 | 844 | 160 |
| 1999-10-02 | vs TOR | 161 | L 3-7 | 89-72 | 1 | 43,049 | Jaret Wright | Pat Hentgen | Pat Hentgen | Jaret Wright | Billy Koch | 1007 | 851 | 156 |
| 1999-10-03 | vs TOR | 162 | L 2-9 | 89-73 | 1 | 43,012 | Dave Burba | David Wells | David Wells | Dave Burba | | 1009 | 860 | 149 |