| 1999-04-05 | vs MON | 1 | L 2-9 | 0-1 | 4 | 43,405 | Francisco Cordova | Dustin Hermanson | Dustin Hermanson | Francisco Cordova | | 2 | 9 | -7 |
| 1999-04-06 | vs MON | 2 | W 8-2 | 1-1 | 4 | 10,051 | Jason Schmidt | Carl Pavano | Jason Schmidt | Carl Pavano | | 10 | 11 | -1 |
| 1999-04-07 | vs MON | 3 | L 3-4 | 1-2 | 5 | 11,377 | Pete Schourek | Javier Vazquez | Ugueth Urbina | Rich Loiselle | | 13 | 15 | -2 |
| 1999-04-09 | vs CHN | 4 | W 2-1 | 2-2 | 5 | 19,721 | Kris Benson | Scott Sanders | Kris Benson | Scott Sanders | Mike Williams | 15 | 16 | -1 |
| 1999-04-10 | vs CHN | 5 | W 9-3 | 3-2 | 2 | 22,479 | Francisco Cordova | Brad Woodall | Scott Sauerbeck | Brad Woodall | | 24 | 19 | 5 |
| 1999-04-11 | vs CHN | 6 | W 9-6 | 4-2 | 1 | 19,384 | Jason Schmidt | Steve Trachsel | Jason Schmidt | Steve Trachsel | | 33 | 25 | 8 |
| 1999-04-13 | vs SLN | 7 | L 2-4 | 4-3 | 3 | 19,724 | Pete Schourek | Kent Bottenfield | Kent Bottenfield | Pete Schourek | Juan Acevedo | 35 | 29 | 6 |
| 1999-04-14 | vs SLN | 8 | L 5-9 | 4-4 | 4 | 18,780 | Kris Benson | Kent Mercker | Manny Aybar | Kris Benson | | 40 | 38 | 2 |
| 1999-04-16 | @ CIN | 9 | L 5-6 | 4-5 | 5 | 17,974 | Jason Schmidt | Brett Tomko | Danny Graves | Jason Christiansen | | 45 | 44 | 1 |
| 1999-04-17 | @ CIN | 10 | W 7-6 | 5-5 | 3 | 15,697 | Chris Peters | Jason Bere | Jason Christiansen | Gabe White | | 52 | 50 | 2 |
| 1999-04-18 | @ CIN | 11 | W 4-2 | 6-5 | 2 | 16,667 | Todd Ritchie | Steve Avery | Rich Loiselle | Danny Graves | Mike Williams | 56 | 52 | 4 |
| 1999-04-19 | @ SDN | 12 | W 3-0 | 7-5 | 2 | 33,616 | Pete Schourek | Stan Spencer | Pete Schourek | Stan Spencer | Jason Christiansen | 59 | 52 | 7 |
| 1999-04-20 | @ SDN | 13 | W 7-3 | 8-5 | 2 | 15,439 | Kris Benson | Matt Clement | Mike Williams | Trevor Hoffman | | 66 | 55 | 11 |
| 1999-04-21 | @ SDN | 14 | L 0-2 | 8-6 | 2 | 13,928 | Jason Schmidt | Andy Ashby | Andy Ashby | Jason Schmidt | Trevor Hoffman | 66 | 57 | 9 |
| 1999-04-23 | vs MIL | 15 | L 1-9 | 8-7 | 2 | 13,850 | Chris Peters | Steve Woodard | Steve Woodard | Chris Peters | | 67 | 66 | 1 |
| 1999-04-24 | vs MIL | 16 | L 3-5 | 8-8 | 3 | 15,809 | Pete Schourek | Cal Eldred | Alberto Reyes | Todd Ritchie | Bob Wickman | 70 | 71 | -1 |
| 1999-04-25 | vs MIL | 17 | L 2-4 | 8-9 | 4 | 17,268 | Kris Benson | Scott Karl | Scott Karl | Kris Benson | Bob Wickman | 72 | 75 | -3 |
| 1999-04-27 | @ ATL | 18 | W 5-3 | 9-9 | 3 | 26,990 | Jason Schmidt | Odalis Perez | Jason Schmidt | Odalis Perez | Mike Williams | 77 | 78 | -1 |
| 1999-04-28 | @ ATL | 19 | L 4-5 | 9-10 | 4 | 29,615 | Chris Peters | Tom Glavine | Tom Glavine | Jason Christiansen | | 81 | 83 | -2 |
| 1999-04-29 | @ ATL | 20 | L 1-8 | 9-11 | 5 | 32,017 | Jose Silva | Greg Maddux | Greg Maddux | Jose Silva | | 82 | 91 | -9 |
| 1999-04-30 | vs COL | 21 | L 2-7 | 9-12 | 5 | 17,466 | Pete Schourek | Pedro Astacio | Pedro Astacio | Pete Schourek | | 84 | 98 | -14 |
| 1999-05-01 | vs COL | 22 | W 9-3 | 10-12 | 4 | 18,599 | Todd Ritchie | Jamey Wright | Todd Ritchie | Jamey Wright | | 93 | 101 | -8 |
| 1999-05-02 | vs COL | 23 | W 8-5 | 11-12 | 4 | 19,215 | Jason Schmidt | John Thomson | Jason Schmidt | John Thomson | Mike Williams | 101 | 106 | -5 |
| 1999-05-03 | vs SFN | 24 | W 9-8 | 12-12 | 4 | 11,099 | Chris Peters | Joe Nathan | Rich Loiselle | Robb Nen | | 110 | 114 | -4 |
| 1999-05-04 | vs SFN | 25 | L 4-7 | 12-13 | 4 | 10,532 | Jose Silva | Russ Ortiz | Russ Ortiz | Jose Silva | | 114 | 121 | -7 |
| 1999-05-05 | vs SFN | 26 | W 4-3 | 13-13 | 4 | 14,358 | Pete Schourek | Shawn Estes | Rich Loiselle | Felix Rodriguez | | 118 | 124 | -6 |
| 1999-05-06 | @ SLN | 27 | W 13-3 | 13-14 | 4 | 36,615 | Todd Ritchie | Donovan Osborne | Todd Ritchie | Donovan Osborne | | 131 | 127 | 4 |
| 1999-05-07 | @ SLN | 28 | L 2-4 | 13-15 | 5 | 39,620 | Jason Schmidt | Darren Oliver | Scott Radinsky | Rich Loiselle | | 133 | 131 | 2 |
| 1999-05-08 | @ SLN | 29 | W 7-0 | 14-15 | 4 | 45,790 | Kris Benson | Jose Jimenez | Kris Benson | Jose Jimenez | | 140 | 131 | 9 |
| 1999-05-09 | @ SLN | 30 | W 12-9 | 14-16 | 5 | 45,458 | Jose Silva | Manny Aybar | Chris Peters | Manny Aybar | Mike Williams | 152 | 140 | 12 |
| 1999-05-10 | @ HOU | 31 | L 0-6 | 14-17 | 5 | 17,064 | Pete Schourek | Mike Hampton | Mike Hampton | Pete Schourek | | 152 | 146 | 6 |
| 1999-05-11 | @ HOU | 32 | L 8-19 | 15-17 | 4 | 18,450 | Todd Ritchie | Sean Bergman | Sean Bergman | Todd Ritchie | | 160 | 165 | -5 |
| 1999-05-12 | @ HOU | 33 | L 2-6 | 15-18 | 5 | 19,792 | Jason Schmidt | Jose Lima | Jose Lima | Jason Schmidt | | 162 | 171 | -9 |
| 1999-05-14 | vs MON | 34 | W 5-3 | 16-18 | 5 | 24,644 | Kris Benson | Dustin Hermanson | Kris Benson | Dustin Hermanson | Mike Williams | 167 | 174 | -7 |
| 1999-05-15 | vs MON | 35 | W 17-6 | 16-19 | 5 | 27,017 | Jose Silva | Carl Pavano | Jose Silva | Carl Pavano | | 184 | 180 | 4 |
| 1999-05-16 | vs MON | 36 | W 9-4 | 17-19 | 5 | 28,882 | Pete Schourek | Javier Vazquez | Pete Schourek | Javier Vazquez | | 193 | 184 | 9 |
| 1999-05-17 | @ ATL | 37 | L 1-2 | 17-20 | 6 | 30,673 | Todd Ritchie | Kevin Millwood | Kevin Millwood | Todd Ritchie | John Rocker | 194 | 186 | 8 |
| 1999-05-18 | @ ATL | 38 | L 4-12 | 18-20 | 6 | 30,858 | Jason Schmidt | Odalis Perez | Odalis Perez | Jason Schmidt | | 198 | 198 | 0 |
| 1999-05-19 | @ ATL | 39 | L 3-7 | 18-21 | 6 | 34,106 | Francisco Cordova | Tom Glavine | Tom Glavine | Francisco Cordova | | 201 | 205 | -4 |
| 1999-05-20 | @ FLO | 40 | L 3-4 | 18-22 | 7 | 11,473 | Kris Benson | Brian Meadows | Antonio Alfonseca | Mike Williams | | 204 | 209 | -5 |
| 1999-05-21 | @ FLO | 41 | L 1-8 | 18-23 | 6 | 16,782 | Pete Schourek | Livan Hernandez | Livan Hernandez | Pete Schourek | | 205 | 217 | -12 |
| 1999-05-22 | @ FLO | 42 | W 11-4 | 18-24 | 6 | 23,121 | Todd Ritchie | Ryan Dempster | Todd Ritchie | Dennis Springer | | 216 | 221 | -5 |
| 1999-05-23 | @ FLO | 43 | W 6-5 | 19-24 | 6 | 19,321 | Jason Schmidt | Alex Fernandez | Jeff Wallace | Vic Darensbourg | Mike Williams | 222 | 226 | -4 |
| 1999-05-24 | vs NYN | 44 | W 7-4 | 20-24 | 6 | 11,880 | Francisco Cordova | Jason Isringhausen | Jose Silva | Jason Isringhausen | Mike Williams | 229 | 230 | -1 |
| 1999-05-25 | vs NYN | 45 | L 3-8 | 20-25 | 6 | 12,029 | Kris Benson | Masato Yoshii | Masato Yoshii | Kris Benson | | 232 | 238 | -6 |
| 1999-05-26 | vs NYN | 46 | L 2-5 | 20-26 | 6 | 13,681 | Pete Schourek | Orel Hershiser | Orel Hershiser | Pete Schourek | John Franco | 234 | 243 | -9 |
| 1999-05-28 | vs HOU | 47 | W 6-5 | 21-26 | 6 | 17,309 | Todd Ritchie | Jose Lima | Todd Ritchie | Jose Lima | Mike Williams | 240 | 248 | -8 |
| 1999-05-29 | vs HOU | 48 | W 5-1 | 22-26 | 6 | 32,426 | Francisco Cordova | Shane Reynolds | Francisco Cordova | Shane Reynolds | | 245 | 249 | -4 |
| 1999-05-30 | vs HOU | 49 | W 7-3 | 23-26 | 6 | 28,905 | Kris Benson | Mike Hampton | Kris Benson | Mike Hampton | | 252 | 252 | 0 |
| 1999-05-31 | vs LAN | 50 | W 5-4 | 24-26 | 6 | 15,924 | Jose Silva | Chan Ho Park | Marc Wilkins | Jamie Arnold | Mike Williams | 257 | 256 | 1 |
| 1999-06-01 | vs LAN | 51 | W 4-2 | 25-26 | 5 | 10,962 | Jason Schmidt | Ismael Valdez | Jason Schmidt | Ismael Valdez | Mike Williams | 261 | 258 | 3 |
| 1999-06-02 | vs LAN | 52 | W 8-4 | 26-26 | 5 | 20,807 | Todd Ritchie | Darren Dreifort | Todd Ritchie | Darren Dreifort | | 269 | 262 | 7 |
| 1999-06-04 | @ CHA | 53 | W 6-3 | 27-26 | 5 | 12,238 | Francisco Cordova | James Baldwin | Marc Wilkins | Bill Simas | | 275 | 265 | 10 |
| 1999-06-05 | @ CHA | 54 | L 5-6 | 27-27 | 6 | 20,066 | Kris Benson | Jim Parque | Jim Parque | Kris Benson | Keith Foulke | 280 | 271 | 9 |
| 1999-06-06 | @ CHA | 55 | L 3-4 | 27-28 | 5 | 26,827 | Jose Silva | Mike Sirotka | Mike Sirotka | Jose Silva | Bob Howry | 283 | 275 | 8 |
| 1999-06-07 | @ DET | 56 | L 4-9 | 27-29 | 5 | 14,280 | Jason Schmidt | Jeff Weaver | Will Brunson | Jason Schmidt | | 287 | 284 | 3 |
| 1999-06-08 | @ DET | 57 | L 4-11 | 28-29 | 5 | 15,270 | Todd Ritchie | Nelson Cruz | Nelson Cruz | Todd Ritchie | | 291 | 295 | -4 |
| 1999-06-09 | @ DET | 58 | W 15-3 | 28-30 | 5 | 15,747 | Francisco Cordova | Brian Moehler | Francisco Cordova | Brian Moehler | | 306 | 298 | 8 |
| 1999-06-11 | vs KCA | 59 | L 3-10 | 29-30 | 5 | 31,052 | Kris Benson | Jose Rosado | Jose Rosado | Kris Benson | | 309 | 308 | 1 |
| 1999-06-12 | vs KCA | 60 | W 9-8 | 30-30 | 5 | 29,569 | Jose Silva | Jeff Suppan | Jason Christiansen | Matt Whisenant | | 318 | 316 | 2 |
| 1999-06-13 | vs KCA | 61 | W 8-4 | 31-30 | 5 | 28,261 | Jason Schmidt | Jay Witasick | Jason Schmidt | Matt Whisenant | Mike Williams | 326 | 320 | 6 |
| 1999-06-15 | @ LAN | 62 | W 11-1 | 32-30 | 5 | 26,284 | Todd Ritchie | Kevin Brown | Todd Ritchie | Kevin Brown | | 337 | 321 | 16 |
| 1999-06-16 | @ LAN | 63 | L 5-6 | 32-31 | 5 | 25,384 | Francisco Cordova | Carlos Perez | Pedro Borbon | Brad Clontz | Jeff Shaw | 342 | 327 | 15 |
| 1999-06-17 | @ LAN | 64 | W 8-3 | 33-31 | 5 | 30,888 | Kris Benson | Chan Ho Park | Kris Benson | Chan Ho Park | | 350 | 330 | 20 |
| 1999-06-18 | @ SDN | 65 | L 2-4 | 33-32 | 5 | 60,799 | Jose Silva | Brian Boehringer | Brian Boehringer | Jose Silva | Trevor Hoffman | 352 | 334 | 18 |
| 1999-06-19 | @ SDN | 66 | L 4-5 | 33-33 | 5 | 33,803 | Jason Schmidt | Heath Murray | Will Cunnane | Jason Schmidt | Trevor Hoffman | 356 | 339 | 17 |
| 1999-06-20 | @ SDN | 67 | L 3-6 | 33-34 | 5 | 25,819 | Todd Ritchie | Matt Clement | Matt Clement | Todd Ritchie | Trevor Hoffman | 359 | 345 | 14 |
| 1999-06-22 | @ PHI | 68 | L 2-3 | 33-35 | 5 | 18,835 | Francisco Cordova | Randy Wolf | Randy Wolf | Francisco Cordova | Wayne Gomes | 361 | 348 | 13 |
| 1999-06-23 | @ PHI | 69 | W 8-6 | 34-35 | 5 | 20,256 | Kris Benson | Paul Byrd | Kris Benson | Paul Byrd | Mike Williams | 369 | 354 | 15 |
| 1999-06-24 | @ PHI | 70 | L 5-7 | 34-36 | 5 | 25,848 | Jose Silva | Curt Schilling | Curt Schilling | Jose Silva | Wayne Gomes | 374 | 361 | 13 |
| 1999-06-25 | @ MIL | 71 | W 5-3 | 35-36 | 5 | 23,958 | Jason Schmidt | Jim Abbott | Jason Schmidt | Jim Abbott | Jason Christiansen | 379 | 364 | 15 |
| 1999-06-26 | @ MIL | 72 | L 4-7 | 35-37 | 5 | 26,590 | Todd Ritchie | Hideo Nomo | Hideo Nomo | Todd Ritchie | Bob Wickman | 383 | 371 | 12 |
| 1999-06-27 | @ MIL | 73 | W 6-5 | 36-37 | 5 | 23,788 | Francisco Cordova | Scott Karl | Francisco Cordova | Scott Karl | Jason Christiansen | 389 | 376 | 13 |
| 1999-06-28 | vs PHI | 74 | W 3-2 | 37-37 | 5 | 14,144 | Kris Benson | Paul Byrd | Greg Hansell | Steve Montgomery | | 392 | 378 | 14 |
| 1999-06-29 | vs PHI | 75 | L 4-7 | 37-38 | 5 | 16,343 | Jose Silva | Curt Schilling | Curt Schilling | Jose Silva | | 396 | 385 | 11 |
| 1999-06-30 | vs PHI | 76 | W 9-1 | 38-38 | 5 | 14,526 | Jason Schmidt | Chad Ogea | Jason Schmidt | Chad Ogea | | 405 | 386 | 19 |
| 1999-07-01 | vs PHI | 77 | W 12-7 | 38-39 | 5 | 11,174 | Todd Ritchie | Robert Person | Todd Ritchie | Robert Person | | 417 | 393 | 24 |
| 1999-07-02 | vs MIL | 78 | L 2-5 | 38-40 | 5 | 20,332 | Francisco Cordova | Scott Karl | Scott Karl | Francisco Cordova | Bob Wickman | 419 | 398 | 21 |
| 1999-07-03 | vs MIL | 79 | L 4-9 | 38-41 | 5 | 28,893 | Kris Benson | Bill Pulsipher | Bill Pulsipher | Kris Benson | | 423 | 407 | 16 |
| 1999-07-04 | vs MIL | 80 | L 3-4 | 38-42 | 6 | 16,553 | Pete Schourek | Steve Woodard | David Weathers | Brad Clontz | Bob Wickman | 426 | 411 | 15 |
| 1999-07-05 | vs CHN | 81 | L 2-5 | 38-43 | 6 | 19,762 | Jason Schmidt | Jon Lieber | Jon Lieber | Jason Schmidt | Rick Aguilera | 428 | 416 | 12 |
| 1999-07-06 | vs CHN | 82 | W 6-1 | 39-43 | 6 | 14,367 | Todd Ritchie | Steve Trachsel | Todd Ritchie | Steve Trachsel | | 434 | 417 | 17 |
| 1999-07-07 | vs CHN | 83 | W 4-1 | 40-43 | 5 | 28,258 | Francisco Cordova | Terry Mulholland | Francisco Cordova | Terry Mulholland | | 438 | 418 | 20 |
| 1999-07-08 | vs CHN | 84 | L 4-9 | 40-44 | 5 | 17,711 | Kris Benson | Dan Serafini | Dan Serafini | Kris Benson | Scott Sanders | 442 | 427 | 15 |
| 1999-07-09 | @ MIN | 85 | L 4-5 | 40-45 | 6 | 13,427 | Jose Silva | Brad Radke | Brad Radke | Jose Silva | Mike Trombley | 446 | 432 | 14 |
| 1999-07-10 | @ MIN | 86 | L 4-5 | 40-46 | 6 | 14,865 | Jason Schmidt | LaTroy Hawkins | Eddie Guardado | Mike Williams | | 450 | 437 | 13 |
| 1999-07-11 | @ MIN | 87 | W 10-2 | 40-47 | 6 | 18,587 | Todd Ritchie | Joe Mays | Todd Ritchie | Joe Mays | | 460 | 439 | 21 |
| 1999-07-15 | vs CLE | 88 | L 0-2 | 40-48 | 6 | 39,620 | Jason Schmidt | Bartolo Colon | Bartolo Colon | Jason Schmidt | Michael Jackson | 460 | 441 | 19 |
| 1999-07-16 | vs CLE | 89 | W 11-3 | 40-49 | 7 | 43,519 | Francisco Cordova | Dave Burba | Francisco Cordova | Dave Burba | | 471 | 444 | 27 |
| 1999-07-17 | vs CLE | 90 | W 13-10 | 41-49 | 6 | 43,299 | Kris Benson | Charles Nagy | Kris Benson | Charles Nagy | Mike Williams | 484 | 454 | 30 |
| 1999-07-18 | vs LAN | 91 | W 6-5 | 42-49 | 6 | 23,855 | Todd Ritchie | Carlos Perez | Scott Sauerbeck | Alan Mills | | 490 | 459 | 31 |
| 1999-07-19 | vs LAN | 92 | L 7-12 | 43-49 | 6 | 14,805 | Jose Silva | Darren Dreifort | Darren Dreifort | Jose Silva | | 497 | 471 | 26 |
| 1999-07-20 | vs LAN | 93 | L 4-8 | 43-50 | 6 | 16,921 | Jason Schmidt | Kevin Brown | Kevin Brown | Brad Clontz | | 501 | 479 | 22 |
| 1999-07-21 | @ CHN | 94 | L 1-2 | 43-51 | 6 | 37,006 | Francisco Cordova | Jon Lieber | Rick Aguilera | Jason Christiansen | | 502 | 481 | 21 |
| 1999-07-22 | @ CHN | 95 | L 3-5 | 43-52 | 6 | 37,112 | Kris Benson | Terry Mulholland | Terry Mulholland | Kris Benson | Terry Adams | 505 | 486 | 19 |
| 1999-07-23 | @ MON | 96 | L 1-5 | 43-53 | 6 | 7,510 | Todd Ritchie | Javier Vazquez | Javier Vazquez | Todd Ritchie | | 506 | 491 | 15 |
| 1999-07-24 | @ MON | 97 | W 7-2 | 44-53 | 6 | 13,396 | Pete Schourek | Jeremy Powell | Pete Schourek | Jeremy Powell | | 513 | 493 | 20 |
| 1999-07-25 | @ MON | 98 | W 6-1 | 45-53 | 6 | 12,244 | Jason Schmidt | Mike Thurman | Jason Schmidt | Steve Kline | | 519 | 494 | 25 |
| 1999-07-26 | @ NYN | 99 | L 5-7 | 45-54 | 6 | 32,010 | Francisco Cordova | Rick Reed | Rick Reed | Francisco Cordova | Turk Wendell | 524 | 501 | 23 |
| 1999-07-27 | @ NYN | 100 | W 5-1 | 46-54 | 6 | 36,337 | Kris Benson | Orel Hershiser | Kris Benson | Orel Hershiser | | 529 | 502 | 27 |
| 1999-07-28 | @ NYN | 101 | L 2-9 | 46-55 | 6 | 42,920 | Todd Ritchie | Kenny Rogers | Dennis Cook | Marc Wilkins | | 531 | 511 | 20 |
| 1999-07-30 | vs FLO | 102 | L 7-8 | 46-56 | 6 | 25,163 | Pete Schourek | Dennis Springer | Brian Edmondson | Greg Hansell | Antonio Alfonseca | 538 | 519 | 19 |
| 1999-07-31 | vs FLO | 103 | W 4-2 | 47-56 | 6 | 33,862 | Jason Schmidt | Vladimir Nunez | Jason Schmidt | Brian Edmondson | Mike Williams | 542 | 521 | 21 |
| 1999-08-01 | vs FLO | 104 | W 2-1 | 48-56 | 6 | 19,071 | Francisco Cordova | Alex Fernandez | Francisco Cordova | Alex Fernandez | | 544 | 522 | 22 |
| 1999-08-03 | vs ATL | 105 | W 7-1 | 49-56 | 6 | 17,154 | Kris Benson | Kevin Millwood | Kris Benson | Kevin Millwood | | 551 | 523 | 28 |
| 1999-08-04 | vs ATL | 106 | W 3-2 | 50-56 | 6 | 17,625 | Todd Ritchie | John Smoltz | Todd Ritchie | John Smoltz | Mike Williams | 554 | 525 | 29 |
| 1999-08-05 | vs ATL | 107 | L 3-6 | 50-57 | 6 | 19,078 | Pete Schourek | Tom Glavine | Mike Remlinger | Greg Hansell | John Rocker | 557 | 531 | 26 |
| 1999-08-06 | vs SLN | 108 | W 5-1 | 51-58 | 9 | 0 | Jimmy Anderson | Jose Jimenez | Jimmy Anderson | Jose Jimenez | Jose Silva | 562 | 532 | 30 |
| 1999-08-06 | vs SLN | 109 | L 1-5 | 51-58 | 9 | 35,521 | Jason Schmidt | Garrett Stephenson | Garrett Stephenson | Jason Schmidt | Rich Croushore | 563 | 537 | 26 |
| 1999-08-07 | vs SLN | 110 | W 3-1 | 52-58 | 5 | 41,063 | Francisco Cordova | Kent Bottenfield | Francisco Cordova | Kent Bottenfield | Mike Williams | 566 | 538 | 28 |
| 1999-08-08 | vs SLN | 111 | W 5-1 | 53-58 | 5 | 31,780 | Kris Benson | Darren Oliver | Kris Benson | Darren Oliver | | 571 | 539 | 32 |
| 1999-08-09 | vs CIN | 112 | L 2-4 | 53-59 | 5 | 13,423 | Todd Ritchie | Denny Neagle | Denny Neagle | Todd Ritchie | Scott Williamson | 573 | 543 | 30 |
| 1999-08-10 | vs CIN | 113 | L 1-6 | 53-60 | 6 | 13,306 | Pete Schourek | Juan Guzman | Juan Guzman | Pete Schourek | | 574 | 549 | 25 |
| 1999-08-11 | vs CIN | 114 | W 5-4 | 54-60 | 5 | 23,728 | Jason Schmidt | Ron Villone | Mike Williams | Scott Williamson | | 579 | 553 | 26 |
| 1999-08-13 | @ HOU | 115 | W 6-5 | 55-60 | 5 | 39,829 | Francisco Cordova | Mike Hampton | Brad Clontz | Trever Miller | Mike Williams | 585 | 558 | 27 |
| 1999-08-14 | @ HOU | 116 | L 1-7 | 55-61 | 6 | 44,868 | Kris Benson | Chris Holt | Chris Holt | Kris Benson | | 586 | 565 | 21 |
| 1999-08-15 | @ HOU | 117 | W 2-0 | 56-61 | 5 | 36,231 | Todd Ritchie | Shane Reynolds | Todd Ritchie | Shane Reynolds | Mike Williams | 588 | 565 | 23 |
| 1999-08-16 | @ CIN | 118 | L 2-9 | 56-62 | 5 | 19,693 | Pete Schourek | Juan Guzman | Juan Guzman | Pete Schourek | | 590 | 574 | 16 |
| 1999-08-17 | @ CIN | 119 | L 4-7 | 56-63 | 5 | 19,118 | Jason Schmidt | Ron Villone | Danny Graves | Mike Williams | | 594 | 581 | 13 |
| 1999-08-18 | @ CIN | 120 | W 12-6 | 56-64 | 5 | 19,733 | Francisco Cordova | Brett Tomko | Francisco Cordova | Brett Tomko | | 606 | 587 | 19 |
| 1999-08-19 | @ CIN | 121 | L 0-1 | 56-65 | 6 | 17,904 | Kris Benson | Pete Harnisch | Pete Harnisch | Kris Benson | Scott Williamson | 606 | 588 | 18 |
| 1999-08-20 | vs ARI | 122 | W 5-4 | 57-65 | 6 | 23,934 | Todd Ritchie | Todd Stottlemyre | Todd Ritchie | Todd Stottlemyre | Mike Williams | 611 | 592 | 19 |
| 1999-08-21 | vs ARI | 123 | L 2-4 | 57-66 | 6 | 31,364 | Jimmy Anderson | Randy Johnson | Randy Johnson | Jimmy Anderson | | 613 | 596 | 17 |
| 1999-08-22 | vs ARI | 124 | L 5-7 | 57-67 | 7 | 25,112 | Jason Schmidt | Omar Daal | Omar Daal | Jason Schmidt | Matt Mantei | 618 | 603 | 15 |
| 1999-08-23 | vs ARI | 125 | L 1-2 | 57-68 | 6 | 11,768 | Francisco Cordova | Armando Reynoso | Armando Reynoso | Francisco Cordova | Matt Mantei | 619 | 605 | 14 |
| 1999-08-24 | vs COL | 126 | L 2-3 | 57-69 | 6 | 13,221 | Kris Benson | Brian Bohanon | Curt Leskanic | Mike Williams | Dave Veres | 621 | 608 | 13 |
| 1999-08-25 | vs COL | 127 | W 9-3 | 58-69 | 7 | 12,535 | Chris Peters | Darryl Kile | Chris Peters | Darryl Kile | | 630 | 611 | 19 |
| 1999-08-26 | vs COL | 128 | W 8-4 | 59-69 | 5 | 12,649 | Jimmy Anderson | Pedro Astacio | Jimmy Anderson | Pedro Astacio | | 638 | 615 | 23 |
| 1999-08-27 | @ SFN | 129 | W 4-1 | 60-69 | 6 | 16,390 | Jason Schmidt | Joe Nathan | Jason Schmidt | Joe Nathan | Mike Williams | 642 | 616 | 26 |
| 1999-08-28 | @ SFN | 130 | L 2-6 | 60-70 | 5 | 32,783 | Francisco Cordova | Mark Gardner | Mark Gardner | Francisco Cordova | | 644 | 622 | 22 |
| 1999-08-29 | @ SFN | 131 | L 3-5 | 60-71 | 5 | 34,020 | Kris Benson | Shawn Estes | Shawn Estes | Kris Benson | Robb Nen | 647 | 627 | 20 |
| 1999-08-30 | @ COL | 132 | W 11-8 | 60-72 | 5 | 41,872 | Chris Peters | Pedro Astacio | Chris Peters | Roberto Ramirez | Mike Williams | 658 | 635 | 23 |
| 1999-08-31 | @ COL | 133 | W 9-8 | 61-72 | 5 | 41,729 | Jimmy Anderson | John Thomson | Mike Williams | David Lee | Jose Silva | 667 | 643 | 24 |
| 1999-09-01 | @ COL | 134 | W 9-8 | 62-72 | 5 | 40,529 | Jason Schmidt | Luther Hackman | Scott Sauerbeck | Dave Veres | Brad Clontz | 676 | 651 | 25 |
| 1999-09-03 | vs SFN | 135 | L 2-12 | 63-72 | 5 | 16,478 | Francisco Cordova | Shawn Estes | Shawn Estes | Francisco Cordova | | 678 | 663 | 15 |
| 1999-09-04 | vs SFN | 136 | L 2-9 | 63-73 | 5 | 19,949 | Kris Benson | Russ Ortiz | Russ Ortiz | Kris Benson | | 680 | 672 | 8 |
| 1999-09-05 | vs SFN | 137 | W 8-4 | 64-73 | 5 | 17,901 | Chris Peters | Kirk Rueter | Chris Peters | Kirk Rueter | | 688 | 676 | 12 |
| 1999-09-06 | vs SDN | 138 | L 3-4 | 64-74 | 5 | 16,663 | Todd Ritchie | Andy Ashby | Andy Ashby | Todd Ritchie | Trevor Hoffman | 691 | 680 | 11 |
| 1999-09-07 | vs SDN | 139 | W 3-1 | 65-74 | 7 | 11,058 | Jason Schmidt | Sterling Hitchcock | Jason Schmidt | Sterling Hitchcock | Jose Silva | 694 | 681 | 13 |
| 1999-09-08 | vs SDN | 140 | L 4-7 | 65-75 | 5 | 10,133 | Francisco Cordova | Woody Williams | Trevor Hoffman | Marc Wilkins | | 698 | 688 | 10 |
| 1999-09-10 | @ SLN | 141 | L 5-11 | 66-75 | 6 | 36,590 | Kris Benson | Kent Bottenfield | Kent Bottenfield | Kris Benson | | 703 | 699 | 4 |
| 1999-09-11 | @ SLN | 142 | W 8-5 | 67-75 | 5 | 46,011 | Chris Peters | Garrett Stephenson | Chris Peters | Jose Jimenez | Jose Silva | 711 | 704 | 7 |
| 1999-09-13 | @ ARI | 143 | L 1-5 | 67-76 | 6 | 32,147 | Jason Schmidt | Omar Daal | Omar Daal | Jason Schmidt | Bobby Chouinard | 712 | 709 | 3 |
| 1999-09-14 | @ ARI | 144 | L 1-2 | 67-77 | 6 | 30,372 | Francisco Cordova | Brian Anderson | Greg Swindell | Marc Wilkins | Matt Mantei | 713 | 711 | 2 |
| 1999-09-15 | @ ARI | 145 | W 5-1 | 68-77 | 6 | 31,294 | Kris Benson | Armando Reynoso | Kris Benson | Armando Reynoso | | 718 | 712 | 6 |
| 1999-09-17 | vs CIN | 146 | W 3-1 | 69-77 | 5 | 21,853 | Todd Ritchie | Ron Villone | Todd Ritchie | Ron Villone | Scott Sauerbeck | 721 | 713 | 8 |
| 1999-09-18 | vs CIN | 147 | L 0-3 | 69-78 | 6 | 21,253 | Chris Peters | Steve Parris | Steve Parris | Chris Peters | | 721 | 716 | 5 |
| 1999-09-19 | vs CIN | 148 | W 8-5 | 70-78 | 5 | 21,183 | Jason Schmidt | Pete Harnisch | Jason Schmidt | Pete Harnisch | Brad Clontz | 729 | 721 | 8 |
| 1999-09-20 | vs HOU | 149 | W 11-5 | 70-79 | 6 | 10,256 | Francisco Cordova | Shane Reynolds | Pete Schourek | Shane Reynolds | | 740 | 726 | 14 |
| 1999-09-21 | vs HOU | 150 | L 3-6 | 70-80 | 6 | 12,745 | Kris Benson | Scott Elarton | Scott Elarton | Kris Benson | Doug Henry | 743 | 732 | 11 |
| 1999-09-22 | vs HOU | 151 | W 3-2 | 71-80 | 6 | 16,647 | Todd Ritchie | Jose Lima | Todd Ritchie | Jose Lima | | 746 | 734 | 12 |
| 1999-09-23 | @ CHN | 152 | L 5-8 | 71-81 | 6 | 36,736 | Chris Peters | Micah Bowie | Micah Bowie | Chris Peters | Rick Aguilera | 751 | 742 | 9 |
| 1999-09-24 | @ CHN | 153 | L 0-9 | 71-82 | 6 | 29,267 | Jason Schmidt | Kyle Farnsworth | Kyle Farnsworth | Jason Schmidt | | 751 | 751 | 0 |
| 1999-09-25 | @ CHN | 154 | L 1-3 | 71-83 | 6 | 39,035 | Francisco Cordova | Jon Lieber | Jon Lieber | Francisco Cordova | | 752 | 754 | -2 |
| 1999-09-26 | @ CHN | 155 | W 8-4 | 72-83 | 6 | 39,663 | Kris Benson | Andrew Lorraine | Scott Sauerbeck | Mark Guthrie | | 760 | 758 | 2 |
| 1999-09-29 | @ MIL | 156 | W 7-5 | 73-84 | 9 | 0 | Todd Ritchie | Steve Woodard | Todd Ritchie | Steve Woodard | Mike Williams | 767 | 763 | 4 |
| 1999-09-29 | @ MIL | 157 | L 2-5 | 73-84 | 9 | 12,464 | Chris Peters | Jason Bere | Jason Bere | Chris Peters | Bob Wickman | 769 | 768 | 1 |
| 1999-09-30 | @ MIL | 158 | W 3-2 | 74-84 | 6 | 12,319 | Pete Schourek | Hideo Nomo | Mike Garcia | Hideo Nomo | Scott Sauerbeck | 772 | 770 | 2 |
| 1999-10-01 | @ NYN | 159 | L 2-3 | 74-85 | 6 | 29,528 | Jason Schmidt | Kenny Rogers | Pat Mahomes | Scott Sauerbeck | | 774 | 773 | 1 |
| 1999-10-02 | @ NYN | 160 | L 0-7 | 74-86 | 6 | 36,878 | Francisco Cordova | Rick Reed | Rick Reed | Francisco Cordova | | 774 | 780 | -6 |
| 1999-10-03 | @ NYN | 161 | L 1-2 | 74-87 | 6 | 50,111 | Kris Benson | Orel Hershiser | Armando Benitez | Greg Hansell | | 775 | 782 | -7 |