| 1999-04-05 | vs MIL | 1 | L 8-10 | 1-0 | 2 | 47,806 | Donovan Osborne | Rafael Roque | David Weathers | Mike Busby | | 8 | 10 | -2 |
| 1999-04-07 | vs MIL | 2 | W 4-1 | 2-0 | 1 | 31,381 | Kent Bottenfield | Steve Woodard | Kent Bottenfield | Steve Woodard | Juan Acevedo | 12 | 11 | 1 |
| 1999-04-08 | vs MIL | 3 | W 9-4 | 3-0 | 1 | 31,142 | Kent Mercker | Jim Abbott | Kent Mercker | Jim Abbott | | 21 | 15 | 6 |
| 1999-04-09 | vs CIN | 4 | L 0-3 | 3-1 | 1 | 35,930 | Darren Oliver | Pete Harnisch | Pete Harnisch | Darren Oliver | | 21 | 18 | 3 |
| 1999-04-10 | vs CIN | 5 | W 4-2 | 4-1 | 1 | 43,759 | Jose Jimenez | Brett Tomko | Juan Acevedo | Scott Williamson | | 25 | 20 | 5 |
| 1999-04-11 | vs CIN | 6 | L 2-4 | 4-2 | 2 | 41,301 | Donovan Osborne | Jason Bere | Jason Bere | Donovan Osborne | Danny Graves | 27 | 24 | 3 |
| 1999-04-13 | @ PIT | 7 | W 4-2 | 5-2 | 1 | 19,724 | Kent Bottenfield | Pete Schourek | Kent Bottenfield | Pete Schourek | Juan Acevedo | 31 | 26 | 5 |
| 1999-04-14 | @ PIT | 8 | W 9-5 | 6-2 | 1 | 18,780 | Kent Mercker | Kris Benson | Manny Aybar | Kris Benson | | 40 | 31 | 9 |
| 1999-04-16 | @ HOU | 9 | W 5-3 | 7-2 | 1 | 40,387 | Darren Oliver | Shane Reynolds | Darren Oliver | Shane Reynolds | Ricky Bottalico | 45 | 34 | 11 |
| 1999-04-17 | @ HOU | 10 | W 8-5 | 8-2 | 1 | 37,662 | Jose Jimenez | Chris Holt | Jose Jimenez | Chris Holt | | 53 | 39 | 14 |
| 1999-04-18 | @ HOU | 11 | L 4-8 | 8-3 | 1 | 34,265 | Donovan Osborne | Mike Hampton | Jay Powell | Lance Painter | | 57 | 47 | 10 |
| 1999-04-19 | @ MIL | 12 | W 6-2 | 9-3 | 1 | 10,575 | Kent Bottenfield | Jim Abbott | Kent Bottenfield | Jim Abbott | | 63 | 49 | 14 |
| 1999-04-20 | @ MIL | 13 | W 8-3 | 10-3 | 1 | 12,365 | Kent Mercker | Scott Karl | Kent Mercker | Scott Karl | | 71 | 52 | 19 |
| 1999-04-21 | @ MIL | 14 | L 1-2 | 10-4 | 1 | 10,959 | Darren Oliver | Rafael Roque | Alberto Reyes | Lance Painter | Bob Wickman | 72 | 54 | 18 |
| 1999-04-23 | @ LAN | 15 | W 12-5 | 10-5 | 1 | 46,687 | Jose Jimenez | Chan Ho Park | Jose Jimenez | Chan Ho Park | | 84 | 59 | 25 |
| 1999-04-24 | @ LAN | 16 | L 1-6 | 10-6 | 1 | 53,964 | Donovan Osborne | Ismael Valdez | Ismael Valdez | Donovan Osborne | | 85 | 65 | 20 |
| 1999-04-25 | @ LAN | 17 | W 6-4 | 11-6 | 1 | 53,857 | Kent Bottenfield | Darren Dreifort | Kent Bottenfield | Darren Dreifort | Juan Acevedo | 91 | 69 | 22 |
| 1999-04-27 | vs COL | 18 | W 7-5 | 12-6 | 1 | 32,389 | Darren Oliver | John Thomson | Darren Oliver | John Thomson | Scott Radinsky | 98 | 74 | 24 |
| 1999-04-28 | vs COL | 19 | L 7-9 | 12-7 | 1 | 34,545 | Jose Jimenez | Brian Bohanon | Brian Bohanon | Jose Jimenez | Dave Veres | 105 | 83 | 22 |
| 1999-04-29 | vs COL | 20 | L 2-6 | 12-8 | 1 | 41,909 | Kent Mercker | Darryl Kile | Darryl Kile | Kent Mercker | | 107 | 89 | 18 |
| 1999-04-30 | @ MON | 21 | L 2-3 | 12-9 | 2 | 11,170 | Kent Bottenfield | Javier Vazquez | Ugueth Urbina | Juan Acevedo | | 109 | 92 | 17 |
| 1999-05-01 | @ MON | 22 | W 16-5 | 12-10 | 3 | 14,511 | Donovan Osborne | Mike Thurman | Donovan Osborne | Mike Thurman | Mike Mohler | 125 | 97 | 28 |
| 1999-05-02 | @ MON | 23 | W 8-7 | 13-10 | 3 | 11,610 | Darren Oliver | Miguel Batista | Juan Acevedo | Ugueth Urbina | Scott Radinsky | 133 | 104 | 29 |
| 1999-05-03 | @ ATL | 24 | L 2-4 | 13-11 | 3 | 37,676 | Jose Jimenez | Tom Glavine | Mike Remlinger | Jose Jimenez | John Rocker | 135 | 108 | 27 |
| 1999-05-04 | @ ATL | 25 | W 9-1 | 14-11 | 3 | 39,161 | Kent Mercker | Greg Maddux | Manny Aybar | Greg Maddux | | 144 | 109 | 35 |
| 1999-05-05 | @ ATL | 26 | L 3-12 | 15-11 | 3 | 44,350 | Kent Bottenfield | John Smoltz | John Smoltz | Kent Bottenfield | | 147 | 121 | 26 |
| 1999-05-06 | vs PIT | 27 | L 3-13 | 16-11 | 2 | 36,615 | Donovan Osborne | Todd Ritchie | Todd Ritchie | Donovan Osborne | | 150 | 134 | 16 |
| 1999-05-07 | vs PIT | 28 | W 4-2 | 17-11 | 3 | 39,620 | Darren Oliver | Jason Schmidt | Scott Radinsky | Rich Loiselle | | 154 | 136 | 18 |
| 1999-05-08 | vs PIT | 29 | L 0-7 | 17-12 | 3 | 45,790 | Jose Jimenez | Kris Benson | Kris Benson | Jose Jimenez | | 154 | 143 | 11 |
| 1999-05-09 | vs PIT | 30 | L 9-12 | 18-12 | 2 | 45,458 | Manny Aybar | Jose Silva | Chris Peters | Manny Aybar | Mike Williams | 163 | 155 | 8 |
| 1999-05-10 | vs PHI | 31 | W 5-2 | 19-12 | 1 | 34,789 | Kent Bottenfield | Carlton Loewer | Kent Bottenfield | Carlton Loewer | Scott Radinsky | 168 | 157 | 11 |
| 1999-05-11 | vs PHI | 32 | L 4-9 | 19-13 | 1 | 32,307 | Kent Mercker | Paul Byrd | Paul Byrd | Kent Mercker | | 172 | 166 | 6 |
| 1999-05-12 | vs PHI | 33 | L 4-8 | 19-14 | 2 | 45,540 | Darren Oliver | Curt Schilling | Curt Schilling | Darren Oliver | | 176 | 174 | 2 |
| 1999-05-14 | vs LAN | 34 | L 3-7 | 19-15 | 3 | 48,036 | Jose Jimenez | Kevin Brown | Kevin Brown | Jose Jimenez | | 179 | 181 | -2 |
| 1999-05-15 | vs LAN | 35 | W 8-5 | 20-15 | 3 | 48,308 | Kent Bottenfield | Chan Ho Park | Kent Bottenfield | Chan Ho Park | | 187 | 186 | 1 |
| 1999-05-16 | vs LAN | 36 | W 5-4 | 21-15 | 1 | 46,097 | Juan Acevedo | Ismael Valdez | Ricky Bottalico | Jeff Shaw | | 192 | 190 | 2 |
| 1999-05-18 | @ SDN | 37 | W 5-2 | 22-15 | 1 | 29,222 | Darren Oliver | Matt Clement | Darren Oliver | Matt Clement | Ricky Bottalico | 197 | 192 | 5 |
| 1999-05-19 | @ SDN | 38 | L 6-7 | 22-16 | 2 | 31,686 | Jose Jimenez | Andy Ashby | Brian Boehringer | Ricky Bottalico | | 203 | 199 | 4 |
| 1999-05-20 | @ SDN | 39 | W 6-4 | 23-16 | 2 | 33,316 | Kent Bottenfield | Sterling Hitchcock | Kent Bottenfield | Sterling Hitchcock | Ricky Bottalico | 209 | 203 | 6 |
| 1999-05-21 | @ LAN | 40 | W 10-6 | 23-17 | 2 | 53,683 | Juan Acevedo | Ismael Valdez | Juan Acevedo | Ismael Valdez | Manny Aybar | 219 | 209 | 10 |
| 1999-05-22 | @ LAN | 41 | L 7-10 | 24-17 | 2 | 54,179 | Clint Sodowsky | Darren Dreifort | Darren Dreifort | Clint Sodowsky | Jeff Shaw | 226 | 219 | 7 |
| 1999-05-23 | @ LAN | 42 | W 8-3 | 25-17 | 2 | 54,514 | Darren Oliver | Carlos Perez | Darren Oliver | Carlos Perez | | 234 | 222 | 12 |
| 1999-05-25 | vs SFN | 43 | L 1-17 | 25-18 | 2 | 45,029 | Jose Jimenez | Chris Brock | Chris Brock | Jose Jimenez | | 235 | 239 | -4 |
| 1999-05-26 | vs SFN | 44 | L 6-7 | 25-19 | 2 | 36,143 | Kent Bottenfield | Kirk Rueter | Kirk Rueter | Kent Bottenfield | Robb Nen | 241 | 246 | -5 |
| 1999-05-27 | vs SFN | 45 | W 3-2 | 26-19 | 2 | 47,829 | Juan Acevedo | Mark Gardner | Heathcliff Slocumb | Jerry Spradlin | | 244 | 248 | -4 |
| 1999-05-28 | @ CHN | 46 | L 3-6 | 26-20 | 2 | 39,287 | Lance Painter | Kevin Tapani | Kevin Tapani | Lance Painter | Rick Aguilera | 247 | 254 | -7 |
| 1999-05-29 | @ CHN | 47 | L 3-4 | 26-21 | 2 | 40,478 | Darren Oliver | Terry Mulholland | Felix Heredia | Ricky Bottalico | | 250 | 258 | -8 |
| 1999-05-30 | @ CHN | 48 | L 4-7 | 26-22 | 2 | 40,425 | Jose Jimenez | Jon Lieber | Jon Lieber | Jose Jimenez | | 254 | 265 | -11 |
| 1999-05-31 | @ FLO | 49 | W 5-2 | 27-22 | 2 | 21,943 | Kent Bottenfield | Brian Meadows | Kent Bottenfield | Brian Meadows | Ricky Bottalico | 259 | 267 | -8 |
| 1999-06-01 | @ FLO | 50 | W 8-4 | 28-22 | 2 | 18,747 | Juan Acevedo | Livan Hernandez | Juan Acevedo | Livan Hernandez | | 267 | 271 | -4 |
| 1999-06-02 | @ FLO | 51 | L 2-10 | 29-22 | 2 | 16,733 | Lance Painter | Ryan Dempster | Ryan Dempster | Lance Painter | | 269 | 281 | -12 |
| 1999-06-03 | @ FLO | 52 | L 2-4 | 29-23 | 2 | 15,751 | Darren Oliver | Alex Fernandez | Braden Looper | Darren Oliver | Matt Mantei | 271 | 285 | -14 |
| 1999-06-04 | @ DET | 53 | L 1-4 | 29-24 | 3 | 40,794 | Jose Jimenez | Brian Moehler | Brian Moehler | Jose Jimenez | Todd Jones | 272 | 289 | -17 |
| 1999-06-05 | @ DET | 54 | W 7-2 | 30-24 | 4 | 43,679 | Kent Bottenfield | Dave Mlicki | Kent Bottenfield | Willie Blair | Ricky Bottalico | 279 | 291 | -12 |
| 1999-06-06 | @ DET | 55 | W 8-4 | 31-24 | 2 | 40,898 | Juan Acevedo | Bryce Florie | Rich Croushore | C.J. Nitkowski | Manny Aybar | 287 | 295 | -8 |
| 1999-06-07 | @ KCA | 56 | W 7-5 | 32-24 | 2 | 37,248 | Lance Painter | Kevin Appier | Heathcliff Slocumb | Kevin Appier | Ricky Bottalico | 294 | 300 | -6 |
| 1999-06-08 | @ KCA | 57 | L 10-11 | 32-25 | 2 | 37,297 | Darren Oliver | Chris Fussell | Scott Service | Darren Oliver | Jeff Montgomery | 304 | 311 | -7 |
| 1999-06-09 | @ KCA | 58 | L 13-17 | 32-26 | 2 | 37,484 | Jose Jimenez | Terry Mathews | Matt Whisenant | Scott Radinsky | | 317 | 328 | -11 |
| 1999-06-11 | vs DET | 59 | L 2-8 | 32-27 | 3 | 41,927 | Kent Bottenfield | Dave Mlicki | Dave Mlicki | Kent Bottenfield | | 319 | 336 | -17 |
| 1999-06-12 | vs DET | 60 | W 8-7 | 33-27 | 3 | 47,716 | Juan Acevedo | Jeff Weaver | Scott Radinsky | Willie Blair | | 327 | 343 | -16 |
| 1999-06-13 | vs DET | 61 | L 1-3 | 33-28 | 3 | 46,269 | Lance Painter | Justin Thompson | Todd Jones | Ricky Bottalico | Doug Brocail | 328 | 346 | -18 |
| 1999-06-14 | vs MON | 62 | L 5-7 | 33-29 | 3 | 47,256 | Darren Oliver | Dan Smith | Anthony Telford | Darren Oliver | Ugueth Urbina | 333 | 353 | -20 |
| 1999-06-15 | vs MON | 63 | W 3-2 | 34-29 | 3 | 34,222 | Jose Jimenez | Mike Thurman | Jose Jimenez | Mike Thurman | Ricky Bottalico | 336 | 355 | -19 |
| 1999-06-16 | vs MON | 64 | W 5-4 | 35-29 | 2 | 37,114 | Kent Bottenfield | Miguel Batista | Kent Bottenfield | Miguel Batista | Ricky Bottalico | 341 | 359 | -18 |
| 1999-06-17 | vs NYN | 65 | L 3-4 | 35-30 | 2 | 37,601 | Kent Mercker | Al Leiter | Al Leiter | Kent Mercker | Dennis Cook | 344 | 363 | -19 |
| 1999-06-18 | vs NYN | 66 | L 2-6 | 35-31 | 4 | 47,191 | Juan Acevedo | Orel Hershiser | Orel Hershiser | Juan Acevedo | Armando Benitez | 346 | 369 | -23 |
| 1999-06-19 | vs NYN | 67 | W 7-6 | 36-31 | 3 | 47,638 | Darren Oliver | Jason Isringhausen | Manny Aybar | Jason Isringhausen | Ricky Bottalico | 353 | 375 | -22 |
| 1999-06-20 | vs NYN | 68 | L 6-9 | 36-32 | 3 | 44,705 | Jose Jimenez | Rick Reed | Rick Reed | Rich Croushore | John Franco | 359 | 384 | -25 |
| 1999-06-21 | vs HOU | 69 | W 5-3 | 37-32 | 2 | 41,506 | Kent Bottenfield | Sean Bergman | Kent Bottenfield | Sean Bergman | Ricky Bottalico | 364 | 387 | -23 |
| 1999-06-22 | vs HOU | 70 | W 4-3 | 38-32 | 2 | 36,481 | Kent Mercker | Jose Lima | Mike Mohler | Jeff McCurry | | 368 | 390 | -22 |
| 1999-06-23 | vs HOU | 71 | L 4-8 | 38-33 | 3 | 36,402 | Juan Acevedo | Shane Reynolds | Shane Reynolds | Juan Acevedo | | 372 | 398 | -26 |
| 1999-06-24 | @ ARI | 72 | L 7-8 | 38-34 | 3 | 41,459 | Darren Oliver | Omar Daal | Vladimir Nunez | Ricky Bottalico | | 379 | 406 | -27 |
| 1999-06-25 | @ ARI | 73 | W 1-0 | 39-34 | 3 | 45,540 | Jose Jimenez | Randy Johnson | Jose Jimenez | Randy Johnson | | 380 | 406 | -26 |
| 1999-06-26 | @ ARI | 74 | W 2-1 | 40-34 | 3 | 48,053 | Kent Bottenfield | Brian Anderson | Manny Aybar | Vladimir Nunez | | 382 | 407 | -25 |
| 1999-06-27 | @ ARI | 75 | L 2-3 | 40-35 | 3 | 44,458 | Kent Mercker | Armando Reynoso | Vladimir Nunez | Ricky Bottalico | | 384 | 410 | -26 |
| 1999-06-29 | @ HOU | 76 | L 4-5 | 40-36 | 3 | 34,797 | Juan Acevedo | Shane Reynolds | Scott Elarton | Manny Aybar | Billy Wagner | 388 | 415 | -27 |
| 1999-06-30 | @ HOU | 77 | L 3-11 | 41-36 | 3 | 42,475 | Jose Jimenez | Mike Hampton | Mike Hampton | Jose Jimenez | | 391 | 426 | -35 |
| 1999-07-01 | @ HOU | 78 | W 10-4 | 41-37 | 3 | 43,727 | Kent Bottenfield | Chris Holt | Kent Bottenfield | Chris Holt | | 401 | 430 | -29 |
| 1999-07-02 | vs ARI | 79 | L 5-9 | 41-38 | 4 | 39,693 | Darren Oliver | Brian Anderson | Brian Anderson | Darren Oliver | | 406 | 439 | -33 |
| 1999-07-03 | vs ARI | 80 | W 2-1 | 42-38 | 3 | 41,278 | Kent Mercker | Armando Reynoso | Lance Painter | Byung-Hyun Kim | | 408 | 440 | -32 |
| 1999-07-04 | vs ARI | 81 | L 5-17 | 43-38 | 3 | 38,041 | Juan Acevedo | Andy Benes | Andy Benes | Rich Croushore | | 413 | 457 | -44 |
| 1999-07-05 | vs ARI | 82 | W 1-0 | 44-38 | 3 | 33,700 | Jose Jimenez | Randy Johnson | Jose Jimenez | Randy Johnson | | 414 | 457 | -43 |
| 1999-07-06 | vs CIN | 83 | W 6-5 | 45-38 | 2 | 40,449 | Kent Bottenfield | Brett Tomko | Kent Bottenfield | Brett Tomko | Ricky Bottalico | 420 | 462 | -42 |
| 1999-07-07 | vs CIN | 84 | W 2-1 | 46-38 | 2 | 34,769 | Darren Oliver | Steve Parris | Rich Croushore | Scott Williamson | | 422 | 463 | -41 |
| 1999-07-08 | vs CIN | 85 | L 5-8 | 46-39 | 2 | 39,603 | Kent Mercker | Pete Harnisch | Pete Harnisch | Kent Mercker | Danny Graves | 427 | 471 | -44 |
| 1999-07-09 | @ SFN | 86 | L 4-5 | 46-40 | 2 | 30,802 | Juan Acevedo | Kirk Rueter | Felix Rodriguez | Manny Aybar | | 431 | 476 | -45 |
| 1999-07-10 | @ SFN | 87 | L 2-4 | 46-41 | 3 | 46,043 | Jose Jimenez | Russ Ortiz | Russ Ortiz | Jose Jimenez | John Johnstone | 433 | 480 | -47 |
| 1999-07-11 | @ SFN | 88 | W 5-4 | 47-41 | 3 | 50,435 | Kent Bottenfield | Mark Gardner | Kent Bottenfield | Mark Gardner | Ricky Bottalico | 438 | 484 | -46 |
| 1999-07-15 | vs CHA | 89 | W 3-2 | 48-41 | 3 | 40,258 | Jose Jimenez | Mike Sirotka | Rich Croushore | Todd Rizzo | | 441 | 486 | -45 |
| 1999-07-16 | vs CHA | 90 | L 8-9 | 48-42 | 4 | 46,909 | Juan Acevedo | Jaime Navarro | Jaime Navarro | Juan Acevedo | Bob Howry | 449 | 495 | -46 |
| 1999-07-17 | vs CHA | 91 | W 8-6 | 49-42 | 3 | 48,650 | Kent Bottenfield | James Baldwin | Garrett Stephenson | Bryan Ward | Ricky Bottalico | 457 | 501 | -44 |
| 1999-07-18 | vs MIN | 92 | L 2-5 | 49-43 | 3 | 45,665 | Darren Oliver | LaTroy Hawkins | LaTroy Hawkins | Darren Oliver | | 459 | 506 | -47 |
| 1999-07-19 | vs MIN | 93 | W 8-4 | 50-43 | 3 | 37,408 | Kent Mercker | Mike Lincoln | Kent Mercker | Mike Lincoln | Ricky Bottalico | 467 | 510 | -43 |
| 1999-07-20 | vs MIN | 94 | L 2-4 | 50-44 | 4 | 35,257 | Larry Luebbers | Brad Radke | Brad Radke | Larry Luebbers | Mike Trombley | 469 | 514 | -45 |
| 1999-07-21 | @ CIN | 95 | L 0-1 | 50-45 | 4 | 33,958 | Jose Jimenez | Ron Villone | Ron Villone | Jose Jimenez | Scott Williamson | 469 | 515 | -46 |
| 1999-07-22 | @ CIN | 96 | W 6-5 | 51-45 | 4 | 35,648 | Kent Bottenfield | Brett Tomko | Lance Painter | Danny Graves | Ricky Bottalico | 475 | 520 | -45 |
| 1999-07-23 | @ COL | 97 | W 6-4 | 52-45 | 4 | 48,824 | Darren Oliver | Roberto Ramirez | Darren Oliver | Roberto Ramirez | Heathcliff Slocumb | 481 | 524 | -43 |
| 1999-07-24 | @ COL | 98 | W 10-2 | 52-46 | 4 | 48,794 | Kent Mercker | Darryl Kile | Kent Mercker | Darryl Kile | | 491 | 526 | -35 |
| 1999-07-25 | @ COL | 99 | W 6-4 | 53-46 | 3 | 48,845 | Larry Luebbers | Pedro Astacio | Larry Luebbers | Pedro Astacio | Manny Aybar | 497 | 530 | -33 |
| 1999-07-26 | @ SFN | 100 | L 8-10 | 54-46 | 3 | 35,936 | Jose Jimenez | Russ Ortiz | Felix Rodriguez | Heathcliff Slocumb | Robb Nen | 505 | 540 | -35 |
| 1999-07-27 | @ SFN | 101 | L 1-2 | 54-47 | 3 | 26,338 | Kent Bottenfield | Kirk Rueter | Kirk Rueter | Kent Bottenfield | John Johnstone | 506 | 542 | -36 |
| 1999-07-28 | @ SFN | 102 | W 6-3 | 55-47 | 3 | 38,740 | Darren Oliver | Livan Hernandez | Darren Oliver | Livan Hernandez | Ricky Bottalico | 512 | 545 | -33 |
| 1999-07-30 | vs COL | 103 | L 4-5 | 55-48 | 3 | 46,208 | Kent Mercker | Pedro Astacio | Pedro Astacio | Manny Aybar | Dave Veres | 516 | 550 | -34 |
| 1999-07-31 | vs COL | 104 | W 6-5 | 56-48 | 3 | 46,849 | Larry Luebbers | Bobby Jones | Lance Painter | Curt Leskanic | Ricky Bottalico | 522 | 555 | -33 |
| 1999-08-01 | vs COL | 105 | L 4-5 | 56-49 | 3 | 45,906 | Jose Jimenez | Brian Bohanon | Brian Bohanon | Jose Jimenez | Dave Veres | 526 | 560 | -34 |
| 1999-08-02 | vs SDN | 106 | W 6-5 | 57-49 | 3 | 35,202 | Kent Bottenfield | Woody Williams | Kent Bottenfield | Woody Williams | Rich Croushore | 532 | 565 | -33 |
| 1999-08-03 | vs SDN | 107 | W 6-0 | 58-49 | 3 | 40,652 | Darren Oliver | Brian Boehringer | Darren Oliver | Brian Boehringer | | 538 | 565 | -27 |
| 1999-08-04 | vs SDN | 108 | W 7-6 | 59-49 | 3 | 43,546 | Kent Mercker | Matt Clement | Heathcliff Slocumb | Donne Wall | Rich Croushore | 545 | 571 | -26 |
| 1999-08-05 | vs SDN | 109 | L 3-10 | 60-49 | 3 | 45,106 | Larry Luebbers | Andy Ashby | Andy Ashby | Larry Luebbers | Trevor Hoffman | 548 | 581 | -33 |
| 1999-08-06 | @ PIT | 110 | L 1-5 | 60-50 | 5 | 0 | Jose Jimenez | Jimmy Anderson | Jimmy Anderson | Jose Jimenez | Jose Silva | 549 | 586 | -37 |
| 1999-08-06 | @ PIT | 111 | W 5-1 | 60-50 | 5 | 35,521 | Garrett Stephenson | Jason Schmidt | Garrett Stephenson | Jason Schmidt | Rich Croushore | 554 | 587 | -33 |
| 1999-08-07 | @ PIT | 112 | L 1-3 | 61-51 | 3 | 41,063 | Kent Bottenfield | Francisco Cordova | Francisco Cordova | Kent Bottenfield | Mike Williams | 555 | 590 | -35 |
| 1999-08-08 | @ PIT | 113 | L 1-5 | 61-52 | 3 | 31,780 | Darren Oliver | Kris Benson | Kris Benson | Darren Oliver | | 556 | 595 | -39 |
| 1999-08-09 | @ PHI | 114 | W 12-6 | 61-53 | 3 | 46,102 | Kent Mercker | Steve Schrenk | Kent Mercker | Steve Schrenk | | 568 | 601 | -33 |
| 1999-08-10 | @ PHI | 115 | L 5-7 | 61-54 | 3 | 48,514 | Jose Jimenez | Robert Person | Jim Poole | Ricky Bottalico | Wayne Gomes | 573 | 608 | -35 |
| 1999-08-11 | @ PHI | 116 | W 5-1 | 62-54 | 3 | 45,830 | Garrett Stephenson | Randy Wolf | Garrett Stephenson | Randy Wolf | Heathcliff Slocumb | 578 | 609 | -31 |
| 1999-08-13 | vs CHN | 117 | W 7-1 | 63-54 | 3 | 48,628 | Kent Bottenfield | Kyle Farnsworth | Kent Bottenfield | Kyle Farnsworth | | 585 | 610 | -25 |
| 1999-08-14 | vs CHN | 118 | L 7-9 | 63-55 | 3 | 48,615 | Darren Oliver | Micah Bowie | Terry Adams | Heathcliff Slocumb | | 592 | 619 | -27 |
| 1999-08-15 | vs CHN | 119 | W 6-5 | 64-55 | 3 | 48,392 | Jose Jimenez | Steve Trachsel | Ricky Bottalico | Terry Adams | | 598 | 624 | -26 |
| 1999-08-16 | vs PHI | 120 | W 4-3 | 65-55 | 3 | 36,741 | Kent Mercker | Randy Wolf | Kent Mercker | Randy Wolf | Ricky Bottalico | 602 | 627 | -25 |
| 1999-08-17 | vs PHI | 121 | W 6-5 | 66-55 | 3 | 38,557 | Garrett Stephenson | Anthony Shumaker | Juan Acevedo | Wayne Gomes | | 608 | 632 | -24 |
| 1999-08-18 | vs PHI | 122 | L 5-6 | 66-56 | 3 | 38,047 | Kent Bottenfield | Chad Ogea | Scott Aldred | Rich Croushore | Wayne Gomes | 613 | 638 | -25 |
| 1999-08-21 | @ NYN | 123 | L 4-7 | 66-57 | 3 | 45,491 | Kent Mercker | Kenny Rogers | Pat Mahomes | Kent Mercker | Armando Benitez | 617 | 645 | -28 |
| 1999-08-22 | @ NYN | 124 | L 7-8 | 66-58 | 4 | 0 | Darren Oliver | Octavio Dotel | Armando Benitez | Ricky Bottalico | | 624 | 653 | -29 |
| 1999-08-22 | @ NYN | 125 | W 7-5 | 66-58 | 4 | 50,139 | Garrett Stephenson | Orel Hershiser | Garrett Stephenson | Orel Hershiser | Juan Acevedo | 631 | 658 | -27 |
| 1999-08-23 | @ MON | 126 | L 7-11 | 68-58 | 3 | 13,668 | Rick Ankiel | Dan Smith | Anthony Telford | Rich Croushore | | 638 | 669 | -31 |
| 1999-08-24 | @ MON | 127 | L 4-8 | 68-59 | 3 | 17,142 | Kent Bottenfield | Javier Vazquez | Javier Vazquez | Kent Bottenfield | Ugueth Urbina | 642 | 677 | -35 |
| 1999-08-25 | @ MON | 128 | L 1-4 | 68-60 | 3 | 15,322 | Larry Luebbers | Jeremy Powell | Jeremy Powell | Larry Luebbers | Ugueth Urbina | 643 | 681 | -38 |
| 1999-08-27 | vs ATL | 129 | L 1-2 | 68-61 | 4 | 46,723 | Garrett Stephenson | Terry Mulholland | Russ Springer | Juan Acevedo | John Rocker | 644 | 683 | -39 |
| 1999-08-28 | vs ATL | 130 | L 0-3 | 68-62 | 3 | 48,068 | Darren Oliver | Kevin Millwood | Mike Remlinger | Lance Painter | John Rocker | 644 | 686 | -42 |
| 1999-08-29 | vs ATL | 131 | L 3-4 | 68-63 | 3 | 45,559 | Rick Ankiel | John Smoltz | Kevin McGlinchy | Juan Acevedo | | 647 | 690 | -43 |
| 1999-08-30 | vs FLO | 132 | L 2-4 | 68-64 | 3 | 33,157 | Kent Bottenfield | Vladimir Nunez | Vladimir Nunez | Kent Bottenfield | Antonio Alfonseca | 649 | 694 | -45 |
| 1999-08-31 | vs FLO | 133 | W 8-1 | 69-64 | 3 | 27,476 | Larry Luebbers | Brian Meadows | Larry Luebbers | Brian Meadows | | 657 | 695 | -38 |
| 1999-09-01 | vs FLO | 134 | W 9-3 | 70-64 | 3 | 28,253 | Garrett Stephenson | Ryan Dempster | Garrett Stephenson | Ryan Dempster | | 666 | 698 | -32 |
| 1999-09-02 | @ MIL | 135 | W 4-3 | 71-64 | 3 | 23,041 | Darren Oliver | Hideo Nomo | Lance Painter | Hector Ramirez | Ricky Bottalico | 670 | 701 | -31 |
| 1999-09-03 | @ MIL | 136 | L 4-5 | 71-65 | 3 | 24,031 | Rick Ankiel | Scott Karl | Rocky Coppinger | Juan Acevedo | | 674 | 706 | -32 |
| 1999-09-04 | @ MIL | 137 | L 2-4 | 71-66 | 3 | 31,347 | Mark Thompson | Bill Pulsipher | Bill Pulsipher | Mark Thompson | Bob Wickman | 676 | 710 | -34 |
| 1999-09-05 | @ MIL | 138 | W 13-9 | 71-67 | 3 | 45,611 | Larry Luebbers | Kyle Peterson | Ricky Bottalico | Bob Wickman | | 689 | 719 | -30 |
| 1999-09-06 | @ ATL | 139 | L 1-4 | 71-68 | 3 | 41,678 | Garrett Stephenson | Greg Maddux | Greg Maddux | Garrett Stephenson | | 690 | 723 | -33 |
| 1999-09-07 | @ ATL | 140 | L 2-3 | 71-69 | 4 | 35,095 | Darren Oliver | Terry Mulholland | Mike Remlinger | Darren Oliver | | 692 | 726 | -34 |
| 1999-09-08 | @ ATL | 141 | L 4-5 | 71-70 | 3 | 36,454 | Rick Ankiel | Kevin Millwood | Kevin Millwood | Rick Ankiel | John Rocker | 696 | 731 | -35 |
| 1999-09-10 | vs PIT | 142 | W 11-5 | 71-71 | 3 | 36,590 | Kent Bottenfield | Kris Benson | Kent Bottenfield | Kris Benson | | 707 | 736 | -29 |
| 1999-09-11 | vs PIT | 143 | L 5-8 | 71-72 | 3 | 46,011 | Garrett Stephenson | Chris Peters | Chris Peters | Jose Jimenez | Jose Silva | 712 | 744 | -32 |
| 1999-09-13 | vs MIL | 144 | L 3-4 | 71-73 | 3 | 28,239 | Mark Thompson | Hideo Nomo | Hideo Nomo | Mark Thompson | Bob Wickman | 715 | 748 | -33 |
| 1999-09-14 | vs MIL | 145 | L 1-4 | 71-74 | 3 | 32,436 | Rick Ankiel | Scott Karl | Scott Karl | Manny Aybar | Bob Wickman | 716 | 752 | -36 |
| 1999-09-15 | vs MIL | 146 | L 8-10 | 72-74 | 3 | 34,672 | Kent Bottenfield | Bill Pulsipher | Hector Ramirez | Juan Acevedo | | 724 | 762 | -38 |
| 1999-09-17 | vs HOU | 147 | W 11-8 | 72-75 | 4 | 37,027 | Garrett Stephenson | Jose Lima | Garrett Stephenson | Jose Lima | Ricky Bottalico | 735 | 770 | -35 |
| 1999-09-18 | vs HOU | 148 | W 13-6 | 72-76 | 4 | 45,536 | Darren Oliver | Mike Hampton | Darren Oliver | Mike Hampton | | 748 | 776 | -28 |
| 1999-09-19 | vs HOU | 149 | L 3-4 | 72-77 | 4 | 41,233 | Jose Jimenez | Chris Holt | Chris Holt | Rich Croushore | Billy Wagner | 751 | 780 | -29 |
| 1999-09-20 | @ CHN | 150 | W 7-2 | 73-77 | 4 | 38,085 | Mark Thompson | Jon Lieber | Mark Thompson | Jon Lieber | | 758 | 782 | -24 |
| 1999-09-21 | @ CHN | 151 | W 7-2 | 74-77 | 3 | 38,254 | Kent Bottenfield | Andrew Lorraine | Kent Bottenfield | Andrew Lorraine | | 765 | 784 | -19 |
| 1999-09-22 | @ CHN | 152 | L 3-5 | 74-78 | 4 | 38,278 | Garrett Stephenson | Steve Trachsel | Steve Trachsel | Garrett Stephenson | Rick Aguilera | 768 | 789 | -21 |
| 1999-09-24 | @ CIN | 153 | L 4-5 | 74-79 | 4 | 36,974 | Darren Oliver | Steve Parris | Steve Parris | Rich Croushore | Danny Graves | 772 | 794 | -22 |
| 1999-09-25 | @ CIN | 154 | L 1-6 | 74-80 | 4 | 38,936 | Jose Jimenez | Denny Neagle | Denny Neagle | Jose Jimenez | Danny Graves | 773 | 800 | -27 |
| 1999-09-26 | @ CIN | 155 | L 5-7 | 74-81 | 4 | 43,613 | Mark Thompson | Juan Guzman | Scott Williamson | Mike Mohler | | 778 | 807 | -29 |
| 1999-09-27 | @ CIN | 156 | L 7-9 | 74-82 | 4 | 28,701 | Garrett Stephenson | Ron Villone | Stan Belinda | Rich Croushore | Dennys Reyes | 785 | 816 | -31 |
| 1999-09-29 | vs SDN | 157 | W 4-3 | 75-82 | 5 | 0 | Darren Oliver | Matt Clement | Darren Oliver | Donne Wall | Lance Painter | 789 | 819 | -30 |
| 1999-09-29 | vs SDN | 158 | W 6-5 | 75-82 | 5 | 37,049 | Jose Jimenez | Andy Ashby | Juan Acevedo | Domingo Guzman | | 795 | 824 | -29 |
| 1999-10-01 | vs CHN | 159 | L 2-3 | 76-83 | 4 | 49,085 | Mark Thompson | Jon Lieber | Jon Lieber | Mark Thompson | | 797 | 827 | -30 |
| 1999-10-02 | vs CHN | 160 | L 3-6 | 76-84 | 4 | 48,841 | Garrett Stephenson | Andrew Lorraine | Andrew Lorraine | Garrett Stephenson | Rick Aguilera | 800 | 833 | -33 |
| 1999-10-03 | vs CHN | 161 | W 9-5 | 77-84 | 4 | 47,998 | Larry Luebbers | Steve Trachsel | Larry Luebbers | Steve Trachsel | Rick Ankiel | 809 | 838 | -29 |