| 1999-04-06 | @ MIN | 1 | L 1-6 | 0-1 | 4 | 45,601 | Pat Hentgen | Brad Radke | Brad Radke | Pat Hentgen | | 1 | 6 | -5 |
| 1999-04-07 | @ MIN | 2 | W 9-3 | 1-1 | 4 | 9,220 | David Wells | Mike Lincoln | David Wells | Mike Lincoln | Roy Halladay | 10 | 9 | 1 |
| 1999-04-08 | @ MIN | 3 | L 9-11 | 2-1 | 3 | 9,431 | Joey Hamilton | Eric Milton | Mike Trombley | Joey Hamilton | Rick Aguilera | 19 | 20 | -1 |
| 1999-04-09 | @ BAL | 4 | W 7-4 | 3-1 | 3 | 36,430 | Kelvim Escobar | Sidney Ponson | Kelvim Escobar | Sidney Ponson | | 26 | 24 | 2 |
| 1999-04-10 | @ BAL | 5 | L 0-1 | 3-2 | 4 | 43,700 | Chris Carpenter | Mike Mussina | Mike Mussina | Chris Carpenter | Mike Timlin | 26 | 25 | 1 |
| 1999-04-11 | @ BAL | 6 | W 9-5 | 4-2 | 3 | 40,273 | Pat Hentgen | Doug Linton | Roy Halladay | Jesse Orosco | | 35 | 30 | 5 |
| 1999-04-12 | vs TBA | 7 | W 7-1 | 5-2 | 2 | 37,160 | David Wells | Tony Saunders | David Wells | Tony Saunders | | 42 | 31 | 11 |
| 1999-04-13 | vs TBA | 8 | L 5-8 | 5-3 | 3 | 23,710 | Joey Hamilton | Bobby Witt | Rick White | Joey Hamilton | Roberto Hernandez | 47 | 39 | 8 |
| 1999-04-14 | vs TBA | 9 | W 7-6 | 6-3 | 2 | 23,847 | Kelvim Escobar | Rolando Arrojo | Graeme Lloyd | Albie Lopez | | 54 | 45 | 9 |
| 1999-04-15 | vs TBA | 10 | W 11-1 | 7-3 | 2 | 23,765 | Chris Carpenter | Julio Santana | Chris Carpenter | Julio Santana | | 65 | 46 | 19 |
| 1999-04-16 | vs BAL | 11 | W 7-6 | 8-3 | 1 | 25,281 | Pat Hentgen | Sidney Ponson | Graeme Lloyd | Ricky Bones | Robert Person | 72 | 52 | 20 |
| 1999-04-17 | vs BAL | 12 | W 7-4 | 9-3 | 1 | 30,739 | David Wells | Doug Linton | David Wells | Doug Linton | Graeme Lloyd | 79 | 56 | 23 |
| 1999-04-18 | vs BAL | 13 | W 6-0 | 10-3 | 1 | 27,126 | Roy Halladay | Juan Guzman | Roy Halladay | Juan Guzman | | 85 | 56 | 29 |
| 1999-04-20 | vs ANA | 14 | W 5-1 | 11-3 | 1 | 23,775 | Kelvim Escobar | Chuck Finley | Kelvim Escobar | Chuck Finley | | 90 | 57 | 33 |
| 1999-04-21 | vs ANA | 15 | W 3-2 | 12-3 | 1 | 23,749 | Chris Carpenter | Omar Olivares | Chris Carpenter | Omar Olivares | Robert Person | 93 | 59 | 34 |
| 1999-04-22 | vs ANA | 16 | W 8-7 | 13-3 | 1 | 28,212 | Pat Hentgen | Tim Belcher | Tom Davey | Mark Petkovsek | Graeme Lloyd | 101 | 66 | 35 |
| 1999-04-23 | @ NYA | 17 | L 4-6 | 13-4 | 1 | 36,529 | David Wells | Orlando Hernandez | Orlando Hernandez | David Wells | Mariano Rivera | 105 | 72 | 33 |
| 1999-04-24 | @ NYA | 18 | L 4-7 | 13-5 | 1 | 46,924 | Roy Halladay | Andy Pettitte | Ramiro Mendoza | Dan Plesac | Mariano Rivera | 109 | 79 | 30 |
| 1999-04-25 | @ NYA | 19 | L 3-4 | 13-6 | 1 | 51,903 | Kelvim Escobar | David Cone | Jason Grimsley | Robert Person | | 112 | 83 | 29 |
| 1999-04-26 | @ ANA | 20 | L 3-4 | 13-7 | 1 | 17,324 | Chris Carpenter | Chuck Finley | Troy Percival | Nerio Rodriguez | | 115 | 87 | 28 |
| 1999-04-27 | @ ANA | 21 | W 10-1 | 14-7 | 1 | 17,899 | Pat Hentgen | Omar Olivares | Pat Hentgen | Omar Olivares | | 125 | 88 | 37 |
| 1999-04-28 | @ ANA | 22 | L 10-12 | 14-8 | 1 | 18,304 | David Wells | Tim Belcher | Mark Petkovsek | Graeme Lloyd | Troy Percival | 135 | 100 | 35 |
| 1999-04-29 | @ ANA | 23 | L 1-17 | 14-9 | 1 | 18,346 | Roy Halladay | Ken Hill | Ken Hill | Roy Halladay | | 136 | 117 | 19 |
| 1999-04-30 | @ SEA | 24 | L 9-11 | 15-9 | 1 | 29,353 | Kelvim Escobar | Jeff Fassero | John Halama | Robert Person | Jose Mesa | 145 | 128 | 17 |
| 1999-05-01 | @ SEA | 25 | W 9-3 | 16-9 | 1 | 35,628 | Chris Carpenter | Jamie Moyer | Chris Carpenter | Jamie Moyer | Tom Davey | 154 | 131 | 23 |
| 1999-05-02 | @ SEA | 26 | L 2-3 | 16-10 | 1 | 31,355 | Pat Hentgen | Mac Suzuki | Ken Cloude | Dan Plesac | | 156 | 134 | 22 |
| 1999-05-03 | @ SEA | 27 | W 16-10 | 17-10 | 1 | 22,304 | David Wells | Freddy Garcia | David Wells | Freddy Garcia | | 172 | 144 | 28 |
| 1999-05-04 | vs OAK | 28 | L 4-13 | 18-10 | 1 | 20,258 | Roy Halladay | Mike Oquist | Mike Oquist | Roy Halladay | Doug Jones | 176 | 157 | 19 |
| 1999-05-05 | vs OAK | 29 | L 2-8 | 18-11 | 1 | 20,314 | Kelvim Escobar | Kenny Rogers | Kenny Rogers | Kelvim Escobar | | 178 | 165 | 13 |
| 1999-05-06 | vs OAK | 30 | L 2-3 | 18-12 | 1 | 20,310 | Chris Carpenter | Gil Heredia | Gil Heredia | Chris Carpenter | Billy Taylor | 180 | 168 | 12 |
| 1999-05-07 | vs TEX | 31 | W 9-6 | 19-12 | 1 | 22,110 | Pat Hentgen | Mark Clark | Pat Hentgen | Mark Clark | Billy Koch | 189 | 174 | 15 |
| 1999-05-08 | vs TEX | 32 | L 3-4 | 19-13 | 2 | 24,642 | David Wells | Mike Morgan | Mike Morgan | David Wells | John Wetteland | 192 | 178 | 14 |
| 1999-05-09 | vs TEX | 33 | L 6-11 | 20-13 | 2 | 20,374 | Roy Halladay | John Burkett | Danny Patterson | Peter Munro | | 198 | 189 | 9 |
| 1999-05-11 | @ KCA | 34 | W 8-2 | 21-13 | 1 | 12,141 | Kelvim Escobar | Jim Pittsley | Kelvim Escobar | Jim Pittsley | | 206 | 191 | 15 |
| 1999-05-12 | @ KCA | 35 | L 1-7 | 21-14 | 1 | 13,073 | Chris Carpenter | Kevin Appier | Kevin Appier | Chris Carpenter | | 207 | 198 | 9 |
| 1999-05-13 | @ KCA | 36 | W 8-2 | 22-14 | 1 | 19,573 | Pat Hentgen | Jose Rosado | Pat Hentgen | Jose Rosado | | 215 | 200 | 15 |
| 1999-05-14 | vs BOS | 37 | L 0-5 | 22-15 | 1 | 22,186 | David Wells | Juan Pena | Juan Pena | David Wells | | 215 | 205 | 10 |
| 1999-05-15 | vs BOS | 38 | L 5-6 | 22-16 | 1 | 24,579 | Roy Halladay | Mark Portugal | John Wasdin | Dan Plesac | Tom Gordon | 220 | 211 | 9 |
| 1999-05-16 | vs BOS | 39 | W 9-6 | 23-16 | 1 | 21,094 | Kelvim Escobar | Pat Rapp | Graeme Lloyd | Kip Gross | | 229 | 217 | 12 |
| 1999-05-17 | vs BOS | 40 | L 7-8 | 23-17 | 2 | 20,395 | Chris Carpenter | Tim Wakefield | John Wasdin | Graeme Lloyd | | 236 | 225 | 11 |
| 1999-05-18 | vs DET | 41 | W 7-5 | 24-17 | 1 | 20,310 | Pat Hentgen | Justin Thompson | Pat Hentgen | Justin Thompson | Billy Koch | 243 | 230 | 13 |
| 1999-05-19 | vs DET | 42 | L 3-7 | 24-18 | 2 | 20,384 | David Wells | Brian Moehler | Brian Moehler | David Wells | | 246 | 237 | 9 |
| 1999-05-20 | vs DET | 43 | W 7-0 | 25-18 | 1 | 21,137 | Roy Halladay | Dave Mlicki | Roy Halladay | Dave Mlicki | | 253 | 237 | 16 |
| 1999-05-21 | @ BOS | 44 | L 2-5 | 25-19 | 2 | 27,284 | Kelvim Escobar | Pat Rapp | Pat Rapp | Kelvim Escobar | | 255 | 242 | 13 |
| 1999-05-22 | @ BOS | 45 | L 4-6 | 25-20 | 2 | 32,038 | Chris Carpenter | Tim Wakefield | Tim Wakefield | Chris Carpenter | Tom Gordon | 259 | 248 | 11 |
| 1999-05-23 | @ BOS | 46 | L 8-10 | 26-20 | 2 | 28,559 | Pat Hentgen | Pedro Martinez | Pedro Martinez | Pat Hentgen | Tom Gordon | 267 | 258 | 9 |
| 1999-05-24 | @ DET | 47 | W 12-6 | 26-21 | 2 | 13,038 | David Wells | Brian Moehler | David Wells | Brian Moehler | | 279 | 264 | 15 |
| 1999-05-25 | @ DET | 48 | W 5-3 | 27-21 | 2 | 13,087 | Roy Halladay | Dave Mlicki | Roy Halladay | Dave Mlicki | Billy Koch | 284 | 267 | 17 |
| 1999-05-26 | @ DET | 49 | W 9-5 | 28-21 | 2 | 14,177 | Kelvim Escobar | Willie Blair | Kelvim Escobar | Willie Blair | Graeme Lloyd | 293 | 272 | 21 |
| 1999-05-28 | vs NYA | 50 | L 6-10 | 29-21 | 1 | 30,355 | Chris Carpenter | Andy Pettitte | Andy Pettitte | Chris Carpenter | | 299 | 282 | 17 |
| 1999-05-29 | vs NYA | 51 | L 3-8 | 29-22 | 1 | 40,175 | Pat Hentgen | David Cone | David Cone | Pat Hentgen | | 302 | 290 | 12 |
| 1999-05-30 | vs NYA | 52 | L 3-8 | 29-23 | 3 | 39,111 | David Wells | Hideki Irabu | Hideki Irabu | David Wells | | 305 | 298 | 7 |
| 1999-06-01 | vs CHA | 53 | L 2-6 | 29-24 | 2 | 20,399 | Kelvim Escobar | Mike Sirotka | Mike Sirotka | Kelvim Escobar | | 307 | 304 | 3 |
| 1999-06-02 | vs CHA | 54 | W 9-7 | 30-24 | 2 | 22,197 | Chris Carpenter | John Snyder | Chris Carpenter | John Snyder | Billy Koch | 316 | 311 | 5 |
| 1999-06-03 | vs CHA | 55 | L 3-10 | 31-24 | 2 | 33,673 | Pat Hentgen | Jaime Navarro | Jaime Navarro | Pat Hentgen | | 319 | 321 | -2 |
| 1999-06-04 | vs MON | 56 | W 6-2 | 32-24 | 2 | 24,147 | David Wells | Mike Thurman | David Wells | Bobby Ayala | | 325 | 323 | 2 |
| 1999-06-05 | vs MON | 57 | L 0-5 | 32-25 | 3 | 28,112 | Joey Hamilton | Miguel Batista | Miguel Batista | Joey Hamilton | | 325 | 328 | -3 |
| 1999-06-06 | vs MON | 58 | W 9-2 | 33-25 | 1 | 24,392 | Kelvim Escobar | Dustin Hermanson | Kelvim Escobar | Dustin Hermanson | | 334 | 330 | 4 |
| 1999-06-07 | @ NYN | 59 | L 2-8 | 33-26 | 1 | 21,457 | Roy Halladay | Orel Hershiser | Orel Hershiser | Roy Halladay | | 336 | 338 | -2 |
| 1999-06-08 | @ NYN | 60 | L 3-11 | 34-26 | 1 | 18,984 | Pat Hentgen | Jason Isringhausen | Jason Isringhausen | Pat Hentgen | | 339 | 349 | -10 |
| 1999-06-09 | @ NYN | 61 | L 3-4 | 34-27 | 1 | 18,254 | David Wells | Rick Reed | Pat Mahomes | Tom Davey | | 342 | 353 | -11 |
| 1999-06-11 | @ PHI | 62 | L 4-8 | 34-28 | 2 | 26,541 | Joey Hamilton | Randy Wolf | Randy Wolf | Joey Hamilton | | 346 | 361 | -15 |
| 1999-06-12 | @ PHI | 63 | L 2-7 | 34-29 | 2 | 20,449 | Kelvim Escobar | Paul Byrd | Paul Byrd | Kelvim Escobar | | 348 | 368 | -20 |
| 1999-06-13 | @ PHI | 64 | W 7-2 | 35-29 | 2 | 28,459 | Pat Hentgen | Curt Schilling | Pat Hentgen | Curt Schilling | | 355 | 370 | -15 |
| 1999-06-15 | vs ANA | 65 | W 13-2 | 35-30 | 3 | 21,165 | David Wells | Tim Belcher | David Wells | Tim Belcher | | 368 | 372 | -4 |
| 1999-06-16 | vs ANA | 66 | W 3-2 | 36-30 | 3 | 22,184 | Joey Hamilton | Steve Sparks | Graeme Lloyd | Scott Schoeneweis | Billy Koch | 371 | 374 | -3 |
| 1999-06-17 | vs ANA | 67 | W 3-0 | 37-30 | 1 | 20,465 | Kelvim Escobar | Ken Hill | Kelvim Escobar | Ken Hill | Billy Koch | 374 | 374 | 0 |
| 1999-06-18 | vs KCA | 68 | L 5-6 | 37-31 | 2 | 24,245 | Pat Hentgen | Jay Witasick | Jay Witasick | Pat Hentgen | Matt Whisenant | 379 | 380 | -1 |
| 1999-06-19 | vs KCA | 69 | W 7-0 | 38-31 | 2 | 23,369 | Roy Halladay | Kevin Appier | Roy Halladay | Kevin Appier | | 386 | 380 | 6 |
| 1999-06-20 | vs KCA | 70 | W 2-1 | 39-31 | 1 | 24,211 | David Wells | Jeff Suppan | David Wells | Scott Service | | 388 | 381 | 7 |
| 1999-06-21 | vs KCA | 71 | W 11-4 | 39-32 | 3 | 20,394 | Joey Hamilton | Chris Fussell | Joey Hamilton | Chris Fussell | | 399 | 385 | 14 |
| 1999-06-22 | vs CLE | 72 | W 4-3 | 40-32 | 2 | 22,197 | Kelvim Escobar | Dwight Gooden | Kelvim Escobar | Dwight Gooden | Billy Koch | 403 | 388 | 15 |
| 1999-06-23 | vs CLE | 73 | L 6-9 | 40-33 | 3 | 23,271 | Pat Hentgen | Charles Nagy | Charles Nagy | Paul Quantrill | | 409 | 397 | 12 |
| 1999-06-24 | vs CLE | 74 | W 3-0 | 41-33 | 3 | 26,117 | Roy Halladay | Dave Burba | Roy Halladay | Dave Burba | Billy Koch | 412 | 397 | 15 |
| 1999-06-25 | @ TBA | 75 | L 4-11 | 42-33 | 3 | 18,633 | David Wells | Wilson Alvarez | Wilson Alvarez | David Wells | | 416 | 408 | 8 |
| 1999-06-26 | @ TBA | 76 | L 2-5 | 42-34 | 3 | 22,062 | Joey Hamilton | Ryan Rupe | Ryan Rupe | Joey Hamilton | Roberto Hernandez | 418 | 413 | 5 |
| 1999-06-27 | @ TBA | 77 | L 0-8 | 42-35 | 3 | 20,556 | Kelvim Escobar | Bobby Witt | Bobby Witt | Kelvim Escobar | | 418 | 421 | -3 |
| 1999-06-28 | @ TBA | 78 | W 3-2 | 43-35 | 3 | 17,727 | Chris Carpenter | Dave Eiland | Chris Carpenter | Dave Eiland | Billy Koch | 421 | 423 | -2 |
| 1999-06-29 | vs BAL | 79 | W 6-5 | 44-35 | 3 | 21,421 | Pat Hentgen | Juan Guzman | John Frascatore | Arthur Rhodes | | 427 | 428 | -1 |
| 1999-06-30 | vs BAL | 80 | W 10-9 | 44-36 | 3 | 21,137 | David Wells | Mike Mussina | John Frascatore | Jesse Orosco | | 437 | 437 | 0 |
| 1999-07-01 | vs BAL | 81 | W 8-6 | 45-36 | 3 | 30,263 | Joey Hamilton | Scott Erickson | John Frascatore | Mike Timlin | Billy Koch | 445 | 443 | 2 |
| 1999-07-02 | vs TBA | 82 | L 7-8 | 45-37 | 3 | 23,109 | Kelvim Escobar | Ryan Rupe | Scott Aldred | Kelvim Escobar | Roberto Hernandez | 452 | 451 | 1 |
| 1999-07-03 | vs TBA | 83 | W 5-0 | 46-37 | 3 | 25,344 | Chris Carpenter | Bobby Witt | Chris Carpenter | Bobby Witt | | 457 | 451 | 6 |
| 1999-07-04 | vs TBA | 84 | W 6-3 | 47-37 | 3 | 24,639 | Pat Hentgen | Dave Eiland | Pat Hentgen | Rick White | Billy Koch | 463 | 454 | 9 |
| 1999-07-06 | @ BAL | 85 | W 4-3 | 48-37 | 3 | 37,939 | David Wells | Scott Erickson | Graeme Lloyd | Mike Timlin | Billy Koch | 467 | 457 | 10 |
| 1999-07-07 | @ BAL | 86 | W 7-6 | 49-37 | 3 | 42,275 | Joey Hamilton | Jason Johnson | Paul Spoljaric | Gabe Molina | Billy Koch | 474 | 463 | 11 |
| 1999-07-08 | @ BAL | 87 | W 11-6 | 49-38 | 3 | 41,738 | Kelvim Escobar | Sidney Ponson | Kelvim Escobar | Sidney Ponson | | 485 | 469 | 16 |
| 1999-07-09 | @ MON | 88 | L 3-4 | 49-39 | 3 | 10,091 | Chris Carpenter | Jeremy Powell | Ugueth Urbina | Graeme Lloyd | | 488 | 473 | 15 |
| 1999-07-10 | @ MON | 89 | W 7-6 | 50-39 | 3 | 15,005 | Pat Hentgen | Dustin Hermanson | Paul Quantrill | Anthony Telford | Billy Koch | 495 | 479 | 16 |
| 1999-07-11 | @ MON | 90 | W 1-0 | 51-39 | 2 | 15,201 | David Wells | Carl Pavano | David Wells | Carl Pavano | | 496 | 479 | 17 |
| 1999-07-15 | vs FLO | 91 | L 6-8 | 51-40 | 3 | 25,072 | Chris Carpenter | Livan Hernandez | Braden Looper | Billy Koch | Antonio Alfonseca | 502 | 487 | 15 |
| 1999-07-16 | vs FLO | 92 | L 2-4 | 51-41 | 3 | 22,449 | Pat Hentgen | Dennis Springer | Dennis Springer | Pat Hentgen | Antonio Alfonseca | 504 | 491 | 13 |
| 1999-07-17 | vs FLO | 93 | W 6-1 | 52-41 | 3 | 27,159 | David Wells | Alex Fernandez | David Wells | Brian Edmondson | | 510 | 492 | 18 |
| 1999-07-18 | vs ATL | 94 | W 3-2 | 53-41 | 2 | 31,137 | Joey Hamilton | Kevin Millwood | Joey Hamilton | Kevin Millwood | Billy Koch | 513 | 494 | 19 |
| 1999-07-19 | vs ATL | 95 | W 8-7 | 54-41 | 1 | 31,064 | Kelvim Escobar | Bruce Chen | John Frascatore | John Hudek | | 521 | 501 | 20 |
| 1999-07-20 | vs ATL | 96 | W 11-6 | 54-42 | 3 | 28,366 | Chris Carpenter | Tom Glavine | Roy Halladay | Tom Glavine | | 532 | 507 | 25 |
| 1999-07-21 | @ CLE | 97 | W 4-3 | 55-42 | 2 | 43,218 | Pat Hentgen | Dave Burba | John Frascatore | Michael Jackson | Billy Koch | 536 | 510 | 26 |
| 1999-07-22 | @ CLE | 98 | W 4-3 | 56-42 | 2 | 43,138 | David Wells | Charles Nagy | David Wells | Charles Nagy | Billy Koch | 540 | 513 | 27 |
| 1999-07-23 | @ CHA | 99 | W 2-1 | 57-42 | 2 | 14,166 | Joey Hamilton | Jim Parque | Joey Hamilton | Jim Parque | Billy Koch | 542 | 514 | 28 |
| 1999-07-24 | @ CHA | 100 | L 5-6 | 57-43 | 2 | 25,674 | Kelvim Escobar | John Snyder | Scott Eyre | Kelvim Escobar | Bob Howry | 547 | 520 | 27 |
| 1999-07-25 | @ CHA | 101 | W 11-3 | 57-44 | 2 | 18,299 | Chris Carpenter | Mike Sirotka | Chris Carpenter | Mike Sirotka | | 558 | 523 | 35 |
| 1999-07-26 | @ CHA | 102 | W 4-3 | 58-44 | 2 | 17,631 | Pat Hentgen | Jaime Navarro | John Frascatore | Bob Howry | Billy Koch | 562 | 526 | 36 |
| 1999-07-27 | vs BOS | 103 | L 9-11 | 59-44 | 2 | 38,631 | David Wells | Bret Saberhagen | Mark Guthrie | Roy Halladay | Tim Wakefield | 571 | 537 | 34 |
| 1999-07-28 | vs BOS | 104 | L 0-8 | 59-45 | 2 | 36,190 | Joey Hamilton | Pat Rapp | Pat Rapp | Joey Hamilton | | 571 | 545 | 26 |
| 1999-07-30 | vs DET | 105 | W 8-2 | 60-45 | 2 | 28,412 | Kelvim Escobar | Jeff Weaver | Kelvim Escobar | Jeff Weaver | | 579 | 547 | 32 |
| 1999-07-31 | vs DET | 106 | W 7-6 | 61-45 | 2 | 29,527 | Chris Carpenter | Dave Mlicki | Roy Halladay | Dave Mlicki | Billy Koch | 586 | 553 | 33 |
| 1999-08-01 | vs DET | 107 | W 8-5 | 62-45 | 1 | 30,105 | Pat Hentgen | Dave Borkowski | Pat Hentgen | Dave Borkowski | Billy Koch | 594 | 558 | 36 |
| 1999-08-02 | @ NYA | 108 | L 1-3 | 62-46 | 2 | 40,825 | David Wells | Andy Pettitte | Andy Pettitte | David Wells | Mariano Rivera | 595 | 561 | 34 |
| 1999-08-03 | @ NYA | 109 | W 3-1 | 63-46 | 1 | 43,110 | Joey Hamilton | David Cone | Joey Hamilton | David Cone | Billy Koch | 598 | 562 | 36 |
| 1999-08-04 | @ NYA | 110 | L 3-8 | 63-47 | 2 | 52,833 | Kelvim Escobar | Hideki Irabu | Hideki Irabu | Kelvim Escobar | | 601 | 570 | 31 |
| 1999-08-06 | @ TEX | 111 | W 5-4 | 64-47 | 1 | 31,664 | Chris Carpenter | Rick Helling | Chris Carpenter | Jeff Zimmerman | Billy Koch | 606 | 574 | 32 |
| 1999-08-07 | @ TEX | 112 | L 0-6 | 64-48 | 2 | 40,329 | Pat Hentgen | Aaron Sele | Aaron Sele | Pat Hentgen | | 606 | 580 | 26 |
| 1999-08-08 | @ TEX | 113 | W 8-7 | 65-48 | 2 | 32,374 | David Wells | John Burkett | John Frascatore | Mike Venafro | Billy Koch | 614 | 587 | 27 |
| 1999-08-09 | @ TEX | 114 | W 19-4 | 65-49 | 2 | 23,235 | Joey Hamilton | Mike Morgan | Joey Hamilton | Mike Morgan | | 633 | 591 | 42 |
| 1999-08-10 | @ MIN | 115 | W 10-6 | 65-50 | 2 | 15,842 | Kelvim Escobar | Brad Radke | Kelvim Escobar | Brad Radke | | 643 | 597 | 46 |
| 1999-08-11 | @ MIN | 116 | W 6-3 | 66-50 | 2 | 15,777 | Chris Carpenter | Eric Milton | Chris Carpenter | Eric Milton | | 649 | 600 | 49 |
| 1999-08-12 | @ MIN | 117 | L 0-3 | 66-51 | 2 | 21,206 | Pat Hentgen | Joe Mays | Joe Mays | Pat Hentgen | Mike Trombley | 649 | 603 | 46 |
| 1999-08-13 | vs OAK | 118 | L 8-9 | 66-52 | 2 | 34,150 | Roy Halladay | Kevin Appier | Kevin Appier | Roy Halladay | Doug Jones | 657 | 612 | 45 |
| 1999-08-14 | vs OAK | 119 | L 5-13 | 67-52 | 2 | 37,113 | Joey Hamilton | Tim Hudson | Tim Hudson | Joey Hamilton | | 662 | 625 | 37 |
| 1999-08-15 | vs OAK | 120 | L 5-9 | 67-53 | 2 | 34,677 | Kelvim Escobar | Mike Oquist | Mike Oquist | Kelvim Escobar | | 667 | 634 | 33 |
| 1999-08-16 | vs SEA | 121 | L 5-7 | 67-54 | 2 | 29,308 | Chris Carpenter | Jamie Moyer | Jamie Moyer | Chris Carpenter | Jose Mesa | 672 | 641 | 31 |
| 1999-08-17 | vs SEA | 122 | L 5-8 | 67-55 | 2 | 30,137 | Pat Hentgen | Paul Abbott | Paul Abbott | Pat Hentgen | Jose Mesa | 677 | 649 | 28 |
| 1999-08-18 | vs SEA | 123 | L 1-5 | 67-56 | 2 | 38,224 | David Wells | Freddy Garcia | Freddy Garcia | David Wells | Jose Paniagua | 678 | 654 | 24 |
| 1999-08-20 | @ OAK | 124 | W 11-0 | 68-56 | 2 | 13,335 | Joey Hamilton | Mike Oquist | Joey Hamilton | Mike Oquist | | 689 | 654 | 35 |
| 1999-08-21 | @ OAK | 125 | L 4-8 | 68-57 | 2 | 26,282 | Chris Carpenter | Omar Olivares | Omar Olivares | Chris Carpenter | | 693 | 662 | 31 |
| 1999-08-22 | @ OAK | 126 | L 3-4 | 68-58 | 2 | 23,907 | Roy Halladay | Gil Heredia | Doug Jones | Billy Koch | | 696 | 666 | 30 |
| 1999-08-23 | @ OAK | 127 | W 9-4 | 69-58 | 2 | 10,047 | David Wells | Kevin Appier | David Wells | Kevin Appier | | 705 | 670 | 35 |
| 1999-08-24 | @ ANA | 128 | W 5-1 | 70-58 | 2 | 21,492 | Pat Hentgen | Ramon Ortiz | Pat Hentgen | Ramon Ortiz | Billy Koch | 710 | 671 | 39 |
| 1999-08-25 | @ ANA | 129 | W 7-2 | 71-58 | 1 | 21,592 | Joey Hamilton | Chuck Finley | Joey Hamilton | Chuck Finley | | 717 | 673 | 44 |
| 1999-08-27 | vs TEX | 130 | L 2-8 | 71-59 | 2 | 30,181 | Chris Carpenter | Rick Helling | Rick Helling | Chris Carpenter | | 719 | 681 | 38 |
| 1999-08-28 | vs TEX | 131 | L 7-9 | 71-60 | 2 | 31,117 | David Wells | Aaron Sele | Aaron Sele | David Wells | John Wetteland | 726 | 690 | 36 |
| 1999-08-29 | vs TEX | 132 | L 2-4 | 71-61 | 3 | 30,502 | Roy Halladay | John Burkett | John Burkett | Roy Halladay | John Wetteland | 728 | 694 | 34 |
| 1999-08-30 | vs MIN | 133 | W 2-1 | 72-61 | 3 | 22,137 | Pat Hentgen | Jason Ryan | Pat Hentgen | Jason Ryan | Billy Koch | 730 | 695 | 35 |
| 1999-08-31 | vs MIN | 134 | L 3-14 | 73-61 | 3 | 23,136 | Joey Hamilton | Brad Radke | Brad Radke | Joey Hamilton | | 733 | 709 | 24 |
| 1999-09-01 | vs MIN | 135 | W 4-0 | 74-61 | 2 | 23,145 | Kelvim Escobar | Eric Milton | Kelvim Escobar | Eric Milton | | 737 | 709 | 28 |
| 1999-09-02 | vs MIN | 136 | W 6-1 | 75-61 | 1 | 22,255 | David Wells | Joe Mays | David Wells | Joe Mays | | 743 | 710 | 33 |
| 1999-09-03 | @ KCA | 137 | W 5-4 | 76-61 | 1 | 13,857 | Roy Halladay | Blake Stein | Paul Quantrill | Alvin Morman | Billy Koch | 748 | 714 | 34 |
| 1999-09-04 | @ KCA | 138 | W 6-3 | 77-61 | 1 | 15,243 | Pat Hentgen | Jeff Suppan | Pat Hentgen | Jeff Suppan | John Frascatore | 754 | 717 | 37 |
| 1999-09-05 | @ KCA | 139 | L 3-6 | 77-62 | 1 | 15,315 | Kelvim Escobar | Jay Witasick | Jay Witasick | Kelvim Escobar | Chris Fussell | 757 | 723 | 34 |
| 1999-09-07 | @ SEA | 140 | L 4-7 | 77-63 | 2 | 39,709 | David Wells | Gil Meche | Gil Meche | David Wells | Jose Mesa | 761 | 730 | 31 |
| 1999-09-08 | @ SEA | 141 | L 3-4 | 77-64 | 3 | 36,971 | Roy Halladay | Jamie Moyer | Jose Mesa | Billy Koch | | 764 | 734 | 30 |
| 1999-09-10 | @ DET | 142 | L 6-7 | 77-65 | 3 | 33,736 | Pat Hentgen | Brian Moehler | Todd Jones | John Frascatore | | 770 | 741 | 29 |
| 1999-09-11 | @ DET | 143 | W 9-5 | 78-65 | 2 | 40,269 | Chris Carpenter | Willie Blair | Paul Spoljaric | Francisco Cordero | | 779 | 746 | 33 |
| 1999-09-12 | @ DET | 144 | W 5-3 | 79-65 | 2 | 39,349 | Kelvim Escobar | Jeff Weaver | Kelvim Escobar | Jeff Weaver | Billy Koch | 784 | 749 | 35 |
| 1999-09-13 | vs NYA | 145 | W 2-1 | 80-65 | 2 | 30,118 | David Wells | Orlando Hernandez | David Wells | Orlando Hernandez | | 786 | 750 | 36 |
| 1999-09-14 | vs NYA | 146 | L 6-10 | 81-65 | 2 | 29,140 | Roy Halladay | David Cone | Ramiro Mendoza | Billy Koch | | 792 | 760 | 32 |
| 1999-09-15 | vs NYA | 147 | L 4-6 | 81-66 | 2 | 29,460 | Pat Hentgen | Andy Pettitte | Andy Pettitte | Pat Hentgen | Mariano Rivera | 796 | 766 | 30 |
| 1999-09-17 | vs CHA | 148 | L 3-7 | 81-67 | 2 | 30,743 | Kelvim Escobar | Kip Wells | Kip Wells | Kelvim Escobar | | 799 | 773 | 26 |
| 1999-09-18 | vs CHA | 149 | L 4-7 | 81-68 | 2 | 28,260 | David Wells | Jim Parque | Jaime Navarro | Paul Quantrill | Bob Howry | 803 | 780 | 23 |
| 1999-09-19 | vs CHA | 150 | L 2-3 | 81-69 | 2 | 27,120 | Roy Halladay | Mike Sirotka | Mike Sirotka | Roy Halladay | Bob Howry | 805 | 783 | 22 |
| 1999-09-21 | @ BOS | 151 | L 0-3 | 81-70 | 2 | 27,799 | Pat Hentgen | Pedro Martinez | Pedro Martinez | Pat Hentgen | | 805 | 786 | 19 |
| 1999-09-22 | @ BOS | 152 | W 14-9 | 81-71 | 4 | 25,345 | Kelvim Escobar | Pat Rapp | Kelvim Escobar | Pat Rapp | | 819 | 795 | 24 |
| 1999-09-23 | @ BOS | 153 | W 7-5 | 82-71 | 3 | 30,780 | David Wells | Kent Mercker | David Wells | Rod Beck | Billy Koch | 826 | 800 | 26 |
| 1999-09-24 | vs CLE | 154 | L 4-18 | 83-71 | 3 | 26,620 | Peter Munro | Jim Brower | Jim Brower | Peter Munro | | 830 | 818 | 12 |
| 1999-09-25 | vs CLE | 155 | L 6-9 | 83-72 | 3 | 32,029 | Paul Spoljaric | Bartolo Colon | Bartolo Colon | Paul Spoljaric | Michael Jackson | 836 | 827 | 9 |
| 1999-09-26 | vs CLE | 156 | L 7-11 | 84-72 | 2 | 34,253 | Pat Hentgen | Dave Burba | Paul Shuey | Billy Koch | | 843 | 838 | 5 |
| 1999-09-28 | @ TBA | 157 | W 8-2 | 85-72 | 3 | 19,781 | David Wells | Dan Wheeler | David Wells | Dan Wheeler | | 851 | 840 | 11 |
| 1999-09-29 | @ TBA | 158 | W 6-2 | 86-72 | 3 | 22,180 | Kelvim Escobar | Bobby Witt | Kelvim Escobar | Bobby Witt | | 857 | 842 | 15 |
| 1999-09-30 | @ CLE | 159 | L 2-9 | 86-73 | 2 | 43,201 | Paul Spoljaric | Bartolo Colon | Bartolo Colon | Paul Spoljaric | | 859 | 851 | 8 |
| 1999-10-01 | @ CLE | 160 | W 8-6 | 87-73 | 2 | 43,040 | Peter Munro | Dwight Gooden | Paul Quantrill | Steve Karsay | Billy Koch | 867 | 857 | 10 |
| 1999-10-02 | @ CLE | 161 | W 7-3 | 88-73 | 2 | 43,049 | Pat Hentgen | Jaret Wright | Pat Hentgen | Jaret Wright | Billy Koch | 874 | 860 | 14 |
| 1999-10-03 | @ CLE | 162 | W 9-2 | 89-73 | 2 | 43,012 | David Wells | Dave Burba | David Wells | Dave Burba | | 883 | 862 | 21 |