| 1999-04-05 | vs CHA | 1 | L 2-8 | 0-1 | 3 | 51,656 | Jeff Fassero | James Baldwin | James Baldwin | Jeff Fassero | | 2 | 8 | -6 |
| 1999-04-06 | vs CHA | 2 | L 3-11 | 1-1 | 4 | 20,435 | Jamie Moyer | Jim Parque | Jim Parque | Jamie Moyer | | 5 | 19 | -14 |
| 1999-04-07 | vs CHA | 3 | W 7-3 | 2-1 | 1 | 21,050 | Freddy Garcia | John Snyder | Freddy Garcia | John Snyder | Jose Mesa | 12 | 22 | -10 |
| 1999-04-09 | vs OAK | 4 | W 6-1 | 3-1 | 1 | 24,823 | Butch Henry | Kenny Rogers | Butch Henry | Kenny Rogers | | 18 | 23 | -5 |
| 1999-04-10 | vs OAK | 5 | L 4-11 | 4-1 | 1 | 35,991 | Jeff Fassero | Gil Heredia | Gil Heredia | Jeff Fassero | | 22 | 34 | -12 |
| 1999-04-11 | vs OAK | 6 | W 11-8 | 4-2 | 1 | 24,036 | Jamie Moyer | Tom Candiotti | Jamie Moyer | Tom Candiotti | | 33 | 42 | -9 |
| 1999-04-12 | vs OAK | 7 | W 6-3 | 5-2 | 1 | 24,650 | Freddy Garcia | Jimmy Haynes | Freddy Garcia | Jimmy Haynes | Jose Mesa | 39 | 45 | -6 |
| 1999-04-13 | vs TEX | 8 | L 6-15 | 6-2 | 1 | 20,710 | Ken Cloude | Mike Morgan | Mike Morgan | Ken Cloude | | 45 | 60 | -15 |
| 1999-04-14 | vs TEX | 9 | L 6-9 | 6-3 | 1 | 20,123 | Butch Henry | John Burkett | Jeff Zimmerman | Jose Paniagua | John Wetteland | 51 | 69 | -18 |
| 1999-04-15 | vs TEX | 10 | L 3-4 | 6-4 | 1 | 22,145 | Jeff Fassero | Rick Helling | Tim Crabtree | John Halama | John Wetteland | 54 | 73 | -19 |
| 1999-04-16 | @ ANA | 11 | L 5-9 | 6-5 | 1 | 39,635 | Jamie Moyer | Tim Belcher | Tim Belcher | Jamie Moyer | | 59 | 82 | -23 |
| 1999-04-17 | @ ANA | 12 | W 4-3 | 7-5 | 1 | 43,752 | Freddy Garcia | Ken Hill | Jose Paniagua | Troy Percival | Jose Mesa | 63 | 85 | -22 |
| 1999-04-18 | @ ANA | 13 | W 8-5 | 8-5 | 1 | 37,465 | Brett Hinchliffe | Steve Sparks | Ken Cloude | Steve Sparks | Jose Mesa | 71 | 90 | -19 |
| 1999-04-20 | @ CHA | 14 | L 1-3 | 8-6 | 1 | 8,980 | Jeff Fassero | Jim Parque | Jim Parque | Jeff Fassero | Bob Howry | 72 | 93 | -21 |
| 1999-04-21 | @ CHA | 15 | L 1-2 | 8-7 | 1 | 9,405 | Jamie Moyer | John Snyder | John Snyder | Jose Paniagua | Bob Howry | 73 | 95 | -22 |
| 1999-04-23 | @ TBA | 16 | L 4-5 | 8-8 | 2 | 20,322 | Freddy Garcia | Bobby Witt | Rick White | John Halama | Roberto Hernandez | 77 | 100 | -23 |
| 1999-04-24 | @ TBA | 17 | W 9-4 | 9-8 | 2 | 26,065 | Butch Henry | Rolando Arrojo | Butch Henry | Rolando Arrojo | | 86 | 104 | -18 |
| 1999-04-25 | @ TBA | 18 | W 6-4 | 10-8 | 2 | 27,163 | Jeff Fassero | Julio Santana | Jose Paniagua | Roberto Hernandez | Jose Mesa | 92 | 108 | -16 |
| 1999-04-26 | vs DET | 19 | L 0-7 | 10-9 | 2 | 25,465 | Jamie Moyer | Brian Moehler | Brian Moehler | Jamie Moyer | | 92 | 115 | -23 |
| 1999-04-27 | vs DET | 20 | L 1-5 | 10-10 | 2 | 19,617 | Brett Hinchliffe | Justin Thompson | Justin Thompson | Brett Hinchliffe | | 93 | 120 | -27 |
| 1999-04-28 | vs DET | 21 | W 8-6 | 11-10 | 2 | 21,708 | Freddy Garcia | Willie Blair | Freddy Garcia | Willie Blair | | 101 | 126 | -25 |
| 1999-04-29 | vs DET | 22 | W 22-6 | 11-11 | 2 | 22,078 | Butch Henry | Dave Mlicki | Ken Cloude | C.J. Nitkowski | | 123 | 132 | -9 |
| 1999-04-30 | vs TOR | 23 | W 11-9 | 11-12 | 2 | 29,353 | Jeff Fassero | Kelvim Escobar | John Halama | Robert Person | Jose Mesa | 134 | 141 | -7 |
| 1999-05-01 | vs TOR | 24 | L 3-9 | 11-13 | 2 | 35,628 | Jamie Moyer | Chris Carpenter | Chris Carpenter | Jamie Moyer | Tom Davey | 137 | 150 | -13 |
| 1999-05-02 | vs TOR | 25 | W 3-2 | 12-13 | 2 | 31,355 | Mac Suzuki | Pat Hentgen | Ken Cloude | Dan Plesac | | 140 | 152 | -12 |
| 1999-05-03 | vs TOR | 26 | L 10-16 | 12-14 | 2 | 22,304 | Freddy Garcia | David Wells | David Wells | Freddy Garcia | | 150 | 168 | -18 |
| 1999-05-05 | @ CLE | 27 | W 6-5 | 13-14 | 2 | 42,991 | Jeff Fassero | Dave Burba | Jeff Fassero | Dave Burba | Jose Mesa | 156 | 173 | -17 |
| 1999-05-06 | @ CLE | 28 | L 4-8 | 13-15 | 2 | 41,962 | Jamie Moyer | Bartolo Colon | Bartolo Colon | Eric Weaver | | 160 | 181 | -21 |
| 1999-05-07 | @ NYA | 29 | L 1-10 | 13-16 | 2 | 38,476 | Mac Suzuki | Hideki Irabu | Hideki Irabu | Mac Suzuki | | 161 | 191 | -30 |
| 1999-05-08 | @ NYA | 30 | W 14-5 | 13-17 | 2 | 41,786 | Freddy Garcia | Orlando Hernandez | Freddy Garcia | Orlando Hernandez | | 175 | 196 | -21 |
| 1999-05-09 | @ NYA | 31 | L 1-6 | 13-18 | 2 | 49,622 | Jeff Fassero | Mike Stanton | Jason Grimsley | Jeff Fassero | | 176 | 202 | -26 |
| 1999-05-10 | @ BOS | 32 | L 4-12 | 14-18 | 2 | 21,660 | Brett Hinchliffe | Pat Rapp | John Wasdin | Brett Hinchliffe | | 180 | 214 | -34 |
| 1999-05-11 | @ BOS | 33 | W 8-5 | 15-18 | 2 | 24,416 | Jamie Moyer | Tim Wakefield | Jamie Moyer | Tim Wakefield | | 188 | 219 | -31 |
| 1999-05-12 | @ BOS | 34 | L 2-9 | 15-19 | 2 | 28,177 | Mac Suzuki | Pedro Martinez | Pedro Martinez | Mac Suzuki | | 190 | 228 | -38 |
| 1999-05-14 | vs KCA | 35 | L 7-12 | 16-19 | 2 | 25,445 | Jeff Fassero | Jeff Suppan | Scott Service | Jeff Fassero | | 197 | 240 | -43 |
| 1999-05-15 | vs KCA | 36 | L 10-11 | 16-20 | 3 | 38,215 | Ken Cloude | Jay Witasick | Jose Santiago | Jose Paniagua | Jeff Montgomery | 207 | 251 | -44 |
| 1999-05-16 | vs KCA | 37 | W 5-1 | 17-20 | 3 | 36,637 | Jamie Moyer | Chris Fussell | Jamie Moyer | Chris Fussell | | 212 | 252 | -40 |
| 1999-05-17 | vs MIN | 38 | W 15-5 | 17-21 | 3 | 25,710 | Mac Suzuki | Eric Milton | John Halama | Eric Milton | | 227 | 257 | -30 |
| 1999-05-18 | vs MIN | 39 | W 10-1 | 18-21 | 3 | 20,486 | Freddy Garcia | Dan Perkins | Freddy Garcia | Dan Perkins | | 237 | 258 | -21 |
| 1999-05-19 | vs MIN | 40 | W 7-0 | 19-21 | 3 | 20,497 | Jeff Fassero | Mike Lincoln | Jeff Fassero | Mike Lincoln | | 244 | 258 | -14 |
| 1999-05-21 | @ KCA | 41 | W 5-2 | 20-21 | 2 | 29,547 | Jamie Moyer | Jay Witasick | Jamie Moyer | Jay Witasick | | 249 | 260 | -11 |
| 1999-05-22 | @ KCA | 42 | W 7-4 | 21-21 | 2 | 36,224 | Ken Cloude | Chris Fussell | Rafael Carmona | Chris Fussell | Jose Mesa | 256 | 264 | -8 |
| 1999-05-23 | @ KCA | 43 | L 4-5 | 21-22 | 2 | 21,373 | Freddy Garcia | Kevin Appier | Matt Whisenant | Jose Paniagua | Jeff Montgomery | 260 | 269 | -9 |
| 1999-05-24 | @ MIN | 44 | L 5-10 | 22-22 | 2 | 12,101 | Jeff Fassero | Dan Perkins | Dan Perkins | Jeff Fassero | | 265 | 279 | -14 |
| 1999-05-25 | @ MIN | 45 | W 15-5 | 22-23 | 3 | 13,875 | John Halama | Gary Rath | John Halama | Gary Rath | | 280 | 284 | -4 |
| 1999-05-26 | @ MIN | 46 | W 11-3 | 22-24 | 4 | 17,022 | Jamie Moyer | LaTroy Hawkins | Jamie Moyer | LaTroy Hawkins | | 291 | 287 | 4 |
| 1999-05-28 | vs TBA | 47 | W 6-1 | 23-24 | 3 | 25,421 | Freddy Garcia | Wilson Alvarez | Freddy Garcia | Wilson Alvarez | | 297 | 288 | 9 |
| 1999-05-29 | vs TBA | 48 | W 11-5 | 23-25 | 4 | 38,093 | Jeff Fassero | Ryan Rupe | Jeff Fassero | Ryan Rupe | | 308 | 293 | 15 |
| 1999-05-30 | vs TBA | 49 | L 7-15 | 24-25 | 3 | 28,090 | Ken Cloude | Bryan Rekar | Bryan Rekar | Ken Cloude | | 315 | 308 | 7 |
| 1999-05-31 | vs BAL | 50 | W 10-6 | 24-26 | 3 | 23,100 | Jamie Moyer | Sidney Ponson | Jamie Moyer | Sidney Ponson | Jose Mesa | 325 | 314 | 11 |
| 1999-06-01 | vs BAL | 51 | L 11-14 | 24-27 | 4 | 21,597 | Freddy Garcia | Juan Guzman | Doug Johns | Freddy Garcia | | 336 | 328 | 8 |
| 1999-06-02 | vs BAL | 52 | W 4-2 | 25-27 | 3 | 21,651 | John Halama | Mike Mussina | Jose Paniagua | Mike Mussina | Jose Mesa | 340 | 330 | 10 |
| 1999-06-04 | @ SDN | 53 | L 2-3 | 25-28 | 3 | 26,060 | Jeff Fassero | Sterling Hitchcock | Donne Wall | Jose Paniagua | Trevor Hoffman | 342 | 333 | 9 |
| 1999-06-05 | @ SDN | 54 | L 2-3 | 25-29 | 3 | 52,539 | Jamie Moyer | Woody Williams | Carlos Reyes | Jose Mesa | | 344 | 336 | 8 |
| 1999-06-06 | @ SDN | 55 | W 4-1 | 26-29 | 3 | 31,761 | Freddy Garcia | Andy Ashby | Freddy Garcia | Andy Ashby | Jose Paniagua | 348 | 337 | 11 |
| 1999-06-07 | @ COL | 56 | W 4-2 | 27-29 | 3 | 40,692 | John Halama | Bobby Jones | John Halama | Bobby Jones | Jose Mesa | 352 | 339 | 13 |
| 1999-06-08 | @ COL | 57 | W 10-5 | 27-30 | 3 | 41,940 | Frankie Rodriguez | Mark Brownson | Frankie Rodriguez | Mark Brownson | Ken Cloude | 362 | 344 | 18 |
| 1999-06-09 | @ COL | 58 | L 11-16 | 27-31 | 4 | 40,671 | Jeff Fassero | Brian Bohanon | Brian Bohanon | Jeff Fassero | | 373 | 360 | 13 |
| 1999-06-11 | vs SFN | 59 | W 7-3 | 28-31 | 3 | 29,527 | Jamie Moyer | Mark Gardner | Jamie Moyer | Mark Gardner | Jose Mesa | 380 | 363 | 17 |
| 1999-06-12 | vs SFN | 60 | L 11-15 | 28-32 | 3 | 35,625 | Freddy Garcia | Kirk Rueter | Kirk Rueter | Freddy Garcia | | 391 | 378 | 13 |
| 1999-06-13 | vs SFN | 61 | L 4-8 | 28-33 | 4 | 33,500 | John Halama | Russ Ortiz | Julian Tavarez | Jose Paniagua | | 395 | 386 | 9 |
| 1999-06-14 | @ DET | 62 | L 7-8 | 28-34 | 4 | 17,291 | Jeff Fassero | Nelson Cruz | Masao Kida | Ken Cloude | | 402 | 394 | 8 |
| 1999-06-15 | @ DET | 63 | W 5-4 | 29-34 | 4 | 16,659 | Frankie Rodriguez | Brian Moehler | Frankie Rodriguez | Brian Moehler | Jose Mesa | 407 | 398 | 9 |
| 1999-06-16 | @ DET | 64 | W 7-1 | 30-34 | 3 | 17,136 | Jamie Moyer | Dave Mlicki | Jamie Moyer | Dave Mlicki | | 414 | 399 | 15 |
| 1999-06-17 | @ DET | 65 | W 4-3 | 31-34 | 3 | 18,415 | Freddy Garcia | Jeff Weaver | Freddy Garcia | Todd Jones | Jose Mesa | 418 | 402 | 16 |
| 1999-06-18 | @ CLE | 66 | W 9-4 | 32-34 | 3 | 43,126 | John Halama | Charles Nagy | John Halama | Charles Nagy | | 427 | 406 | 21 |
| 1999-06-19 | @ CLE | 67 | L 6-10 | 33-34 | 2 | 43,205 | Melvin Bunch | Dave Burba | Dave Burba | Allen Watson | Michael Jackson | 433 | 416 | 17 |
| 1999-06-20 | @ CLE | 68 | L 5-13 | 34-34 | 2 | 43,070 | Frankie Rodriguez | Jaret Wright | Jaret Wright | Frankie Rodriguez | | 438 | 429 | 9 |
| 1999-06-21 | @ CLE | 69 | L 3-4 | 34-35 | 2 | 43,093 | Jamie Moyer | Bartolo Colon | Steve Karsay | Jose Mesa | | 441 | 433 | 8 |
| 1999-06-22 | vs ANA | 70 | L 2-4 | 34-36 | 3 | 26,153 | Freddy Garcia | Steve Sparks | Mark Petkovsek | Freddy Garcia | Troy Percival | 443 | 437 | 6 |
| 1999-06-23 | vs ANA | 71 | W 8-3 | 35-36 | 2 | 25,087 | John Halama | Ken Hill | John Halama | Ken Hill | Frankie Rodriguez | 451 | 440 | 11 |
| 1999-06-24 | vs ANA | 72 | L 7-12 | 36-36 | 2 | 26,431 | Jeff Fassero | Chuck Finley | Scott Schoeneweis | Jose Mesa | Mark Petkovsek | 458 | 452 | 6 |
| 1999-06-25 | vs TEX | 73 | L 4-14 | 37-36 | 2 | 30,490 | Paul Abbott | Ryan Glynn | Ryan Glynn | Frankie Rodriguez | | 462 | 466 | -4 |
| 1999-06-26 | vs TEX | 74 | W 5-4 | 38-36 | 2 | 37,992 | Jamie Moyer | Rick Helling | Jose Paniagua | Mike Venafro | Jose Mesa | 467 | 470 | -3 |
| 1999-06-27 | vs TEX | 75 | W 5-2 | 39-36 | 2 | 56,530 | Freddy Garcia | Aaron Sele | Freddy Garcia | Aaron Sele | Jose Mesa | 472 | 472 | 0 |
| 1999-06-29 | @ OAK | 76 | W 2-1 | 40-36 | 2 | 11,762 | John Halama | Mike Oquist | Jose Paniagua | T.J. Mathews | Jose Mesa | 474 | 473 | 1 |
| 1999-06-30 | @ OAK | 77 | L 5-14 | 41-36 | 2 | 17,224 | Jeff Fassero | Tim Hudson | Tim Hudson | Jeff Fassero | | 479 | 487 | -8 |
| 1999-07-01 | @ OAK | 78 | L 4-5 | 41-37 | 2 | 11,632 | Frankie Rodriguez | Jimmy Haynes | Billy Taylor | Jose Paniagua | | 483 | 492 | -9 |
| 1999-07-02 | @ TEX | 79 | L 6-7 | 41-38 | 2 | 39,677 | Jamie Moyer | Rick Helling | John Wetteland | Ken Cloude | | 489 | 499 | -10 |
| 1999-07-03 | @ TEX | 80 | W 13-12 | 42-38 | 2 | 46,674 | Freddy Garcia | Aaron Sele | Jose Paniagua | Tim Crabtree | Jose Mesa | 502 | 511 | -9 |
| 1999-07-04 | @ TEX | 81 | W 6-0 | 43-38 | 2 | 47,204 | John Halama | Mike Morgan | John Halama | Mike Morgan | | 508 | 511 | -3 |
| 1999-07-05 | @ ANA | 82 | W 10-0 | 44-38 | 2 | 36,987 | Jeff Fassero | Shigetoshi Hasegawa | Jeff Fassero | Shigetoshi Hasegawa | | 518 | 511 | 7 |
| 1999-07-06 | @ ANA | 83 | L 2-8 | 44-39 | 2 | 22,444 | Gil Meche | Mike Fyhrie | Mark Petkovsek | Frankie Rodriguez | | 520 | 519 | 1 |
| 1999-07-07 | @ ANA | 84 | L 3-10 | 45-39 | 2 | 23,623 | Jamie Moyer | Steve Sparks | Steve Sparks | Jamie Moyer | | 523 | 529 | -6 |
| 1999-07-09 | @ LAN | 85 | L 0-5 | 45-40 | 2 | 44,653 | Freddy Garcia | Ismael Valdez | Ismael Valdez | Freddy Garcia | | 523 | 534 | -11 |
| 1999-07-10 | @ LAN | 86 | L 1-2 | 45-41 | 2 | 50,813 | John Halama | Kevin Brown | Jeff Shaw | Jose Paniagua | | 524 | 536 | -12 |
| 1999-07-11 | @ LAN | 87 | L 3-14 | 46-41 | 2 | 43,211 | Jeff Fassero | Darren Dreifort | Darren Dreifort | Jeff Fassero | Onan Masaoka | 527 | 550 | -23 |
| 1999-07-15 | vs SDN | 88 | L 2-3 | 46-42 | 2 | 44,607 | Jamie Moyer | Andy Ashby | Will Cunnane | Jose Mesa | Dan Miceli | 529 | 553 | -24 |
| 1999-07-16 | vs SDN | 89 | L 1-2 | 46-43 | 2 | 43,252 | Jeff Fassero | Sterling Hitchcock | Sterling Hitchcock | Jeff Fassero | Trevor Hoffman | 530 | 555 | -25 |
| 1999-07-17 | vs SDN | 90 | W 9-1 | 47-43 | 2 | 44,077 | Freddy Garcia | Woody Williams | Freddy Garcia | Woody Williams | | 539 | 556 | -17 |
| 1999-07-18 | vs ARI | 91 | W 8-7 | 48-43 | 2 | 44,705 | John Halama | Omar Daal | Jose Mesa | Byung-Hyun Kim | | 547 | 563 | -16 |
| 1999-07-19 | vs ARI | 92 | W 7-5 | 49-43 | 2 | 44,287 | Gil Meche | Brian Anderson | Gil Meche | Brian Anderson | | 554 | 568 | -14 |
| 1999-07-20 | vs ARI | 93 | L 0-6 | 49-44 | 2 | 44,884 | Frankie Rodriguez | Randy Johnson | Randy Johnson | Damaso Marte | | 554 | 574 | -20 |
| 1999-07-21 | vs OAK | 94 | L 3-13 | 50-44 | 2 | 42,223 | Jeff Fassero | Gil Heredia | Gil Heredia | Jeff Fassero | | 557 | 587 | -30 |
| 1999-07-22 | vs OAK | 95 | W 5-4 | 51-44 | 2 | 44,311 | Freddy Garcia | Tim Hudson | Paul Abbott | Doug Jones | | 562 | 591 | -29 |
| 1999-07-23 | @ MIN | 96 | L 4-5 | 51-45 | 2 | 20,014 | John Halama | LaTroy Hawkins | Hector Carrasco | Jose Paniagua | | 566 | 596 | -30 |
| 1999-07-24 | @ MIN | 97 | L 3-10 | 52-45 | 2 | 30,138 | Gil Meche | Mark Redman | Bob Wells | Gil Meche | | 569 | 606 | -37 |
| 1999-07-25 | @ MIN | 98 | W 4-3 | 53-45 | 2 | 21,621 | Jamie Moyer | Brad Radke | Jamie Moyer | Brad Radke | Jose Mesa | 573 | 609 | -36 |
| 1999-07-27 | @ KCA | 99 | L 7-9 | 53-46 | 2 | 18,232 | Jeff Fassero | Kevin Appier | Kevin Appier | Jeff Fassero | Scott Service | 580 | 618 | -38 |
| 1999-07-28 | @ KCA | 100 | L 3-5 | 53-47 | 2 | 17,476 | Freddy Garcia | Jose Rosado | Jose Rosado | Freddy Garcia | Scott Service | 583 | 623 | -40 |
| 1999-07-29 | @ KCA | 101 | W 8-4 | 54-47 | 2 | 20,147 | John Halama | Jeff Suppan | John Halama | Jeff Suppan | | 591 | 627 | -36 |
| 1999-07-30 | vs BAL | 102 | W 7-4 | 55-47 | 2 | 44,931 | Gil Meche | Jason Johnson | Gil Meche | Jason Johnson | Jose Mesa | 598 | 631 | -33 |
| 1999-07-31 | vs BAL | 103 | W 5-2 | 56-47 | 2 | 45,139 | Jamie Moyer | Sidney Ponson | Jamie Moyer | Sidney Ponson | Jose Mesa | 603 | 633 | -30 |
| 1999-08-01 | vs BAL | 104 | W 3-1 | 57-47 | 2 | 45,149 | Jeff Fassero | Mike Mussina | Paul Abbott | Mike Mussina | Jose Mesa | 606 | 634 | -28 |
| 1999-08-02 | vs TBA | 105 | W 4-0 | 58-47 | 2 | 45,118 | Freddy Garcia | Mickey Callaway | Freddy Garcia | Mickey Callaway | Jose Paniagua | 610 | 634 | -24 |
| 1999-08-03 | vs TBA | 106 | W 5-2 | 59-47 | 2 | 37,180 | John Halama | Ryan Rupe | John Halama | Ryan Rupe | Jose Mesa | 615 | 636 | -21 |
| 1999-08-04 | vs TBA | 107 | L 1-7 | 59-48 | 2 | 42,336 | Gil Meche | Dave Eiland | Dave Eiland | Gil Meche | | 616 | 643 | -27 |
| 1999-08-05 | vs NYA | 108 | L 4-7 | 59-49 | 2 | 45,190 | Jamie Moyer | Roger Clemens | Roger Clemens | Jamie Moyer | Mariano Rivera | 620 | 650 | -30 |
| 1999-08-06 | vs NYA | 109 | L 8-11 | 60-49 | 2 | 45,262 | Jeff Fassero | Orlando Hernandez | Allen Watson | Jeff Fassero | Mariano Rivera | 628 | 661 | -33 |
| 1999-08-07 | vs NYA | 110 | L 0-1 | 60-50 | 2 | 45,202 | Freddy Garcia | Andy Pettitte | Andy Pettitte | Freddy Garcia | Mariano Rivera | 628 | 662 | -34 |
| 1999-08-08 | vs NYA | 111 | L 3-9 | 60-51 | 2 | 45,195 | John Halama | David Cone | David Cone | John Halama | | 631 | 671 | -40 |
| 1999-08-09 | vs CHA | 112 | W 6-4 | 61-51 | 2 | 42,978 | Gil Meche | John Snyder | Gil Meche | John Snyder | Jose Mesa | 637 | 675 | -38 |
| 1999-08-10 | vs CHA | 113 | W 4-3 | 62-51 | 2 | 43,696 | Jamie Moyer | Mike Sirotka | Jamie Moyer | Bob Howry | | 641 | 678 | -37 |
| 1999-08-11 | vs CHA | 114 | W 11-2 | 62-52 | 2 | 45,194 | Paul Abbott | Jaime Navarro | Paul Abbott | Jaime Navarro | | 652 | 680 | -28 |
| 1999-08-13 | @ BOS | 115 | L 6-11 | 63-52 | 3 | 33,653 | Freddy Garcia | Pat Rapp | Derek Lowe | Jeff Fassero | | 658 | 691 | -33 |
| 1999-08-14 | @ BOS | 116 | L 2-13 | 64-52 | 2 | 33,253 | John Halama | Bryce Florie | Pedro Martinez | John Halama | | 660 | 704 | -44 |
| 1999-08-15 | @ BOS | 117 | W 4-3 | 65-52 | 2 | 32,460 | Gil Meche | Mark Portugal | Gil Meche | Mark Portugal | Jose Mesa | 664 | 707 | -43 |
| 1999-08-16 | @ TOR | 118 | W 7-5 | 66-52 | 2 | 29,308 | Jamie Moyer | Chris Carpenter | Jamie Moyer | Chris Carpenter | Jose Mesa | 671 | 712 | -41 |
| 1999-08-17 | @ TOR | 119 | W 8-5 | 67-52 | 2 | 30,137 | Paul Abbott | Pat Hentgen | Paul Abbott | Pat Hentgen | Jose Mesa | 679 | 717 | -38 |
| 1999-08-18 | @ TOR | 120 | W 5-1 | 68-52 | 2 | 38,224 | Freddy Garcia | David Wells | Freddy Garcia | David Wells | Jose Paniagua | 684 | 718 | -34 |
| 1999-08-20 | vs CLE | 121 | L 4-7 | 68-53 | 2 | 44,915 | John Halama | Bartolo Colon | Bartolo Colon | John Halama | Michael Jackson | 688 | 725 | -37 |
| 1999-08-21 | vs CLE | 122 | L 0-6 | 68-54 | 2 | 44,891 | Gil Meche | Dave Burba | Dave Burba | Gil Meche | | 688 | 731 | -43 |
| 1999-08-22 | vs CLE | 123 | L 4-7 | 68-55 | 2 | 44,941 | Jamie Moyer | Chris Haney | David Riske | Jose Mesa | Michael Jackson | 692 | 738 | -46 |
| 1999-08-23 | vs CLE | 124 | W 4-1 | 69-55 | 2 | 44,689 | Paul Abbott | Charles Nagy | Paul Abbott | Charles Nagy | Jose Mesa | 696 | 739 | -43 |
| 1999-08-24 | vs DET | 125 | W 5-0 | 70-55 | 2 | 42,517 | Freddy Garcia | Willie Blair | Freddy Garcia | Willie Blair | | 701 | 739 | -38 |
| 1999-08-25 | vs DET | 126 | W 3-2 | 71-55 | 2 | 43,789 | John Halama | Brian Moehler | John Halama | Brian Moehler | Jose Mesa | 704 | 741 | -37 |
| 1999-08-27 | @ NYA | 127 | L 0-8 | 71-56 | 2 | 51,985 | Gil Meche | Roger Clemens | Roger Clemens | Gil Meche | | 704 | 749 | -45 |
| 1999-08-28 | @ NYA | 128 | L 1-2 | 71-57 | 2 | 54,787 | Jamie Moyer | Orlando Hernandez | Mariano Rivera | Jose Paniagua | | 705 | 751 | -46 |
| 1999-08-29 | @ NYA | 129 | L 5-11 | 72-57 | 2 | 52,493 | Paul Abbott | Andy Pettitte | Andy Pettitte | Paul Abbott | Mariano Rivera | 710 | 762 | -52 |
| 1999-08-30 | @ CHA | 130 | W 5-2 | 73-58 | 3 | 0 | Freddy Garcia | Jim Parque | Freddy Garcia | Jim Parque | Jose Mesa | 715 | 764 | -49 |
| 1999-08-30 | @ CHA | 131 | W 14-6 | 73-58 | 3 | 17,190 | Ken Cloude | Carlos Castillo | Ken Cloude | Carlos Castillo | Frankie Rodriguez | 729 | 770 | -41 |
| 1999-08-31 | @ CHA | 132 | W 11-4 | 73-59 | 2 | 12,579 | John Halama | John Snyder | John Halama | John Snyder | | 740 | 774 | -34 |
| 1999-09-01 | @ CHA | 133 | W 3-2 | 74-59 | 2 | 12,472 | Gil Meche | Mike Sirotka | Gil Meche | Mike Sirotka | Jose Mesa | 743 | 776 | -33 |
| 1999-09-03 | vs BOS | 134 | W 2-1 | 75-59 | 2 | 44,471 | Jamie Moyer | Pat Rapp | Jamie Moyer | Derek Lowe | | 745 | 777 | -32 |
| 1999-09-04 | vs BOS | 135 | L 0-4 | 75-60 | 2 | 44,597 | Paul Abbott | Pedro Martinez | Pedro Martinez | Paul Abbott | | 745 | 781 | -36 |
| 1999-09-05 | vs BOS | 136 | L 7-9 | 75-61 | 2 | 44,019 | Freddy Garcia | Mark Portugal | Rich Garces | Jose Paniagua | Derek Lowe | 752 | 790 | -38 |
| 1999-09-06 | vs BOS | 137 | L 2-3 | 75-62 | 3 | 44,246 | John Halama | Kent Mercker | Bryce Florie | John Halama | Derek Lowe | 754 | 793 | -39 |
| 1999-09-07 | vs TOR | 138 | W 7-4 | 76-62 | 2 | 39,709 | Gil Meche | David Wells | Gil Meche | David Wells | Jose Mesa | 761 | 797 | -36 |
| 1999-09-08 | vs TOR | 139 | W 4-3 | 77-62 | 2 | 36,971 | Jamie Moyer | Roy Halladay | Jose Mesa | Billy Koch | | 765 | 800 | -35 |
| 1999-09-10 | @ BAL | 140 | L 4-5 | 77-63 | 2 | 43,209 | Paul Abbott | Doug Linton | Alberto Reyes | Robert Ramsay | | 769 | 805 | -36 |
| 1999-09-11 | @ BAL | 141 | L 2-4 | 77-64 | 2 | 47,903 | Freddy Garcia | Doug Johns | Doug Johns | Freddy Garcia | Mike Timlin | 771 | 809 | -38 |
| 1999-09-12 | @ BAL | 142 | L 1-4 | 77-65 | 2 | 44,891 | John Halama | Scott Erickson | Scott Erickson | John Halama | | 772 | 813 | -41 |
| 1999-09-13 | @ BAL | 143 | L 4-5 | 77-66 | 2 | 40,756 | Gil Meche | Sidney Ponson | B.J. Ryan | Jose Mesa | | 776 | 818 | -42 |
| 1999-09-14 | @ TBA | 144 | W 5-1 | 78-66 | 2 | 15,154 | Jamie Moyer | Rolando Arrojo | Jamie Moyer | Rolando Arrojo | | 781 | 819 | -38 |
| 1999-09-15 | @ TBA | 145 | L 4-8 | 78-67 | 2 | 15,542 | Ken Cloude | Wilson Alvarez | Albie Lopez | Frankie Rodriguez | | 785 | 827 | -42 |
| 1999-09-16 | @ TBA | 146 | W 5-3 | 79-67 | 2 | 15,817 | Freddy Garcia | Ryan Rupe | Freddy Garcia | Esteban Yan | Jose Mesa | 790 | 830 | -40 |
| 1999-09-17 | vs MIN | 147 | W 4-3 | 80-67 | 2 | 44,315 | John Halama | Eric Milton | Paul Abbott | Mike Trombley | | 794 | 833 | -39 |
| 1999-09-18 | vs MIN | 148 | W 5-0 | 81-67 | 2 | 44,511 | Gil Meche | Joe Mays | Gil Meche | Joe Mays | | 799 | 833 | -34 |
| 1999-09-19 | vs MIN | 149 | L 1-2 | 81-68 | 2 | 44,362 | Jamie Moyer | LaTroy Hawkins | LaTroy Hawkins | Jamie Moyer | Mike Trombley | 800 | 835 | -35 |
| 1999-09-20 | vs KCA | 150 | L 9-10 | 82-68 | 2 | 33,254 | Robert Ramsay | Blake Stein | Jose Santiago | Brett Hinchliffe | Jeff Montgomery | 809 | 845 | -36 |
| 1999-09-21 | vs KCA | 151 | W 13-3 | 82-69 | 2 | 34,179 | Freddy Garcia | Jeff Suppan | Freddy Garcia | Jeff Suppan | Frankie Rodriguez | 822 | 848 | -26 |
| 1999-09-22 | vs KCA | 152 | L 6-12 | 83-69 | 2 | 38,016 | John Halama | Jay Witasick | Jay Witasick | John Halama | | 828 | 860 | -32 |
| 1999-09-24 | vs ANA | 153 | W 4-3 | 84-69 | 2 | 44,403 | Gil Meche | Brian Cooper | Jose Mesa | Troy Percival | | 832 | 863 | -31 |
| 1999-09-25 | vs ANA | 154 | L 3-7 | 84-70 | 2 | 44,308 | Jamie Moyer | Chuck Finley | Chuck Finley | Jamie Moyer | | 835 | 870 | -35 |
| 1999-09-26 | vs ANA | 155 | W 3-2 | 85-70 | 2 | 44,485 | Robert Ramsay | Ramon Ortiz | Tom Davey | Shigetoshi Hasegawa | | 838 | 872 | -34 |
| 1999-09-27 | @ TEX | 156 | L 2-3 | 85-71 | 2 | 32,118 | Freddy Garcia | Rick Helling | Tim Crabtree | Steve Sinclair | John Wetteland | 840 | 875 | -35 |
| 1999-09-28 | @ TEX | 157 | L 0-10 | 85-72 | 2 | 30,292 | John Halama | Jeff Fassero | Mike Morgan | John Halama | | 840 | 885 | -45 |
| 1999-09-29 | @ TEX | 158 | W 7-3 | 86-72 | 2 | 39,474 | Gil Meche | Aaron Sele | Gil Meche | Aaron Sele | | 847 | 888 | -41 |
| 1999-09-30 | @ TEX | 159 | L 0-7 | 86-73 | 2 | 28,214 | Brett Hinchliffe | John Burkett | John Burkett | Brett Hinchliffe | | 847 | 895 | -48 |
| 1999-10-01 | @ OAK | 160 | L 1-5 | 86-74 | 2 | 14,414 | Robert Ramsay | Kevin Appier | Kevin Appier | Robert Ramsay | Doug Jones | 848 | 900 | -52 |
| 1999-10-02 | @ OAK | 161 | W 10-2 | 86-75 | 2 | 24,054 | Freddy Garcia | Brett Laxton | Freddy Garcia | Brett Laxton | | 858 | 902 | -44 |
| 1999-10-03 | @ OAK | 162 | L 1-3 | 86-76 | 2 | 25,400 | John Halama | Ron Mahay | Ron Mahay | John Halama | Jason Isringhausen | 859 | 905 | -46 |