| 1999-04-05 | vs ARI | 1 | W 8-6 | 1-0 | 1 | 53,109 | Kevin Brown | Randy Johnson | Jeff Shaw | John Frascatore | | 8 | 6 | 2 |
| 1999-04-06 | vs ARI | 2 | W 3-2 | 2-0 | 1 | 33,139 | Chan Ho Park | Todd Stottlemyre | Alan Mills | Brian Anderson | | 11 | 8 | 3 |
| 1999-04-07 | vs ARI | 3 | W 6-4 | 3-0 | 1 | 29,042 | Ismael Valdez | Andy Benes | Ismael Valdez | Andy Benes | Jeff Shaw | 17 | 12 | 5 |
| 1999-04-08 | vs COL | 4 | L 2-4 | 3-1 | 1 | 27,879 | Carlos Perez | Brian Bohanon | Brian Bohanon | Carlos Perez | Dave Veres | 19 | 16 | 3 |
| 1999-04-09 | vs COL | 5 | W 9-6 | 4-1 | 1 | 39,997 | Darren Dreifort | John Thomson | Darren Dreifort | John Thomson | Jeff Shaw | 28 | 22 | 6 |
| 1999-04-10 | vs COL | 6 | W 2-0 | 5-1 | 1 | 44,503 | Kevin Brown | Darryl Kile | Kevin Brown | Darryl Kile | Jeff Shaw | 30 | 22 | 8 |
| 1999-04-12 | @ ARI | 7 | L 6-12 | 6-1 | 1 | 46,929 | Chan Ho Park | Andy Benes | Andy Benes | Chan Ho Park | | 36 | 34 | 2 |
| 1999-04-13 | @ ARI | 8 | L 6-7 | 6-2 | 1 | 31,197 | Ismael Valdez | Armando Reynoso | Bobby Chouinard | Dave Mlicki | | 42 | 41 | 1 |
| 1999-04-14 | @ ARI | 9 | L 2-6 | 6-3 | 1 | 30,561 | Carlos Perez | Omar Daal | Omar Daal | Carlos Perez | | 44 | 47 | -3 |
| 1999-04-15 | @ ARI | 10 | W 8-1 | 7-3 | 1 | 36,105 | Darren Dreifort | Randy Johnson | Darren Dreifort | Randy Johnson | | 52 | 48 | 4 |
| 1999-04-16 | @ SDN | 11 | L 0-3 | 7-4 | 1 | 48,943 | Kevin Brown | Andy Ashby | Andy Ashby | Kevin Brown | | 52 | 51 | 1 |
| 1999-04-17 | @ SDN | 12 | W 7-3 | 8-4 | 1 | 56,568 | Chan Ho Park | Sterling Hitchcock | Chan Ho Park | Carlos Reyes | | 59 | 54 | 5 |
| 1999-04-18 | @ SDN | 13 | L 3-4 | 8-5 | 1 | 51,341 | Ismael Valdez | Woody Williams | Dan Miceli | Onan Masaoka | Trevor Hoffman | 62 | 58 | 4 |
| 1999-04-19 | vs ATL | 14 | L 3-11 | 9-5 | 1 | 31,454 | Carlos Perez | John Smoltz | John Smoltz | Carlos Perez | | 65 | 69 | -4 |
| 1999-04-20 | vs ATL | 15 | W 5-4 | 10-5 | 1 | 37,717 | Darren Dreifort | Kevin Millwood | Darren Dreifort | Kevin Millwood | Jeff Shaw | 70 | 73 | -3 |
| 1999-04-21 | vs ATL | 16 | L 4-11 | 11-5 | 1 | 31,902 | Kevin Brown | Odalis Perez | Mike Remlinger | Jeff Kubenka | | 74 | 84 | -10 |
| 1999-04-23 | vs SLN | 17 | L 5-12 | 12-5 | 1 | 46,687 | Chan Ho Park | Jose Jimenez | Jose Jimenez | Chan Ho Park | | 79 | 96 | -17 |
| 1999-04-24 | vs SLN | 18 | W 6-1 | 13-5 | 1 | 53,964 | Ismael Valdez | Donovan Osborne | Ismael Valdez | Donovan Osborne | | 85 | 97 | -12 |
| 1999-04-25 | vs SLN | 19 | L 4-6 | 13-6 | 1 | 53,857 | Darren Dreifort | Kent Bottenfield | Kent Bottenfield | Darren Dreifort | Juan Acevedo | 89 | 103 | -14 |
| 1999-04-27 | @ MIL | 20 | W 3-2 | 14-6 | 1 | 11,028 | Kevin Brown | Rafael Roque | Kevin Brown | Rafael Roque | Jeff Shaw | 92 | 105 | -13 |
| 1999-04-28 | @ MIL | 21 | W 3-2 | 15-6 | 1 | 10,669 | Chan Ho Park | Steve Woodard | Chan Ho Park | Steve Woodard | Jeff Shaw | 95 | 107 | -12 |
| 1999-04-29 | @ MIL | 22 | W 10-4 | 15-7 | 2 | 11,441 | Ismael Valdez | Cal Eldred | Ismael Valdez | Cal Eldred | | 105 | 111 | -6 |
| 1999-04-30 | @ PHI | 23 | W 4-3 | 16-7 | 1 | 20,024 | Carlos Perez | Paul Byrd | Carlos Perez | Paul Byrd | Jeff Shaw | 109 | 114 | -5 |
| 1999-05-01 | @ PHI | 24 | W 12-6 | 16-8 | 1 | 22,053 | Darren Dreifort | Paul Spoljaric | Darren Dreifort | Paul Spoljaric | | 121 | 120 | 1 |
| 1999-05-02 | @ PHI | 25 | L 3-12 | 17-8 | 1 | 34,608 | Kevin Brown | Curt Schilling | Curt Schilling | Kevin Brown | | 124 | 132 | -8 |
| 1999-05-03 | @ MON | 26 | W 7-0 | 18-8 | 1 | 5,132 | Chan Ho Park | Dustin Hermanson | Chan Ho Park | Dustin Hermanson | | 131 | 132 | -1 |
| 1999-05-04 | @ MON | 27 | L 1-2 | 18-9 | 1 | 5,846 | Ismael Valdez | Carl Pavano | Carl Pavano | Ismael Valdez | Ugueth Urbina | 132 | 134 | -2 |
| 1999-05-05 | @ MON | 28 | W 8-2 | 19-9 | 1 | 5,518 | Jamie Arnold | Javier Vazquez | Jamie Arnold | Javier Vazquez | | 140 | 136 | 4 |
| 1999-05-07 | vs FLO | 29 | L 3-6 | 19-10 | 1 | 54,009 | Darren Dreifort | Dennis Springer | Dennis Springer | Darren Dreifort | Matt Mantei | 143 | 142 | 1 |
| 1999-05-08 | vs FLO | 30 | W 8-1 | 20-10 | 1 | 36,595 | Kevin Brown | Livan Hernandez | Kevin Brown | Livan Hernandez | | 151 | 143 | 8 |
| 1999-05-09 | vs FLO | 31 | L 4-6 | 20-11 | 1 | 29,397 | Chan Ho Park | Jesus Sanchez | Brian Edmondson | Pedro Borbon | Matt Mantei | 155 | 149 | 6 |
| 1999-05-10 | vs CHN | 32 | W 4-3 | 21-11 | 1 | 32,925 | Ismael Valdez | Steve Trachsel | Ismael Valdez | Steve Trachsel | Jeff Shaw | 159 | 152 | 7 |
| 1999-05-11 | vs CHN | 33 | L 5-10 | 22-11 | 1 | 30,470 | Carlos Perez | Kyle Farnsworth | Kyle Farnsworth | Carlos Perez | | 164 | 162 | 2 |
| 1999-05-12 | vs CHN | 34 | W 3-2 | 23-11 | 1 | 40,007 | Darren Dreifort | Kevin Tapani | Jamie Arnold | Rod Beck | | 167 | 164 | 3 |
| 1999-05-14 | @ SLN | 35 | W 7-3 | 24-11 | 1 | 48,036 | Kevin Brown | Jose Jimenez | Kevin Brown | Jose Jimenez | | 174 | 167 | 7 |
| 1999-05-15 | @ SLN | 36 | L 5-8 | 24-12 | 1 | 48,308 | Chan Ho Park | Kent Bottenfield | Kent Bottenfield | Chan Ho Park | | 179 | 175 | 4 |
| 1999-05-16 | @ SLN | 37 | L 4-5 | 24-13 | 1 | 46,097 | Ismael Valdez | Juan Acevedo | Ricky Bottalico | Jeff Shaw | | 183 | 180 | 3 |
| 1999-05-18 | vs HOU | 38 | L 3-11 | 25-13 | 1 | 27,067 | Carlos Perez | Jose Lima | Jose Lima | Carlos Perez | | 186 | 191 | -5 |
| 1999-05-19 | vs HOU | 39 | W 5-2 | 26-13 | 1 | 26,360 | Kevin Brown | Shane Reynolds | Kevin Brown | Shane Reynolds | | 191 | 193 | -2 |
| 1999-05-20 | vs HOU | 40 | L 3-4 | 26-14 | 1 | 40,780 | Chan Ho Park | Mike Hampton | Billy Wagner | Jeff Shaw | | 194 | 197 | -3 |
| 1999-05-21 | vs SLN | 41 | L 6-10 | 27-14 | 1 | 53,683 | Ismael Valdez | Juan Acevedo | Juan Acevedo | Ismael Valdez | Manny Aybar | 200 | 207 | -7 |
| 1999-05-22 | vs SLN | 42 | W 10-7 | 27-15 | 1 | 54,179 | Darren Dreifort | Clint Sodowsky | Darren Dreifort | Clint Sodowsky | Jeff Shaw | 210 | 214 | -4 |
| 1999-05-23 | vs SLN | 43 | L 3-8 | 27-16 | 1 | 54,514 | Carlos Perez | Darren Oliver | Darren Oliver | Carlos Perez | | 213 | 222 | -9 |
| 1999-05-25 | @ CIN | 44 | L 2-3 | 27-17 | 1 | 18,203 | Kevin Brown | Steve Parris | Steve Parris | Kevin Brown | Danny Graves | 215 | 225 | -10 |
| 1999-05-26 | @ CIN | 45 | W 9-3 | 28-17 | 1 | 19,273 | Chan Ho Park | Brett Tomko | Chan Ho Park | Brett Tomko | | 224 | 228 | -4 |
| 1999-05-27 | @ CIN | 46 | W 4-3 | 29-17 | 1 | 21,836 | Ismael Valdez | Pete Harnisch | Ismael Valdez | Pete Harnisch | Jeff Shaw | 228 | 231 | -3 |
| 1999-05-28 | @ ATL | 47 | L 2-4 | 29-18 | 1 | 41,953 | Darren Dreifort | Odalis Perez | Odalis Perez | Darren Dreifort | John Rocker | 230 | 235 | -5 |
| 1999-05-29 | @ ATL | 48 | W 2-1 | 30-18 | 1 | 49,258 | Carlos Perez | Tom Glavine | Carlos Perez | Tom Glavine | Jeff Shaw | 232 | 236 | -4 |
| 1999-05-30 | @ ATL | 49 | W 5-4 | 31-18 | 1 | 47,166 | Kevin Brown | Greg Maddux | Pedro Borbon | Mike Remlinger | Jeff Shaw | 237 | 240 | -3 |
| 1999-05-31 | @ PIT | 50 | L 4-5 | 31-19 | 1 | 15,924 | Chan Ho Park | Jose Silva | Marc Wilkins | Jamie Arnold | Mike Williams | 241 | 245 | -4 |
| 1999-06-01 | @ PIT | 51 | L 2-4 | 31-20 | 1 | 10,962 | Ismael Valdez | Jason Schmidt | Jason Schmidt | Ismael Valdez | Mike Williams | 243 | 249 | -6 |
| 1999-06-02 | @ PIT | 52 | L 4-8 | 31-21 | 1 | 20,807 | Darren Dreifort | Todd Ritchie | Todd Ritchie | Darren Dreifort | | 247 | 257 | -10 |
| 1999-06-04 | vs ANA | 53 | W 5-4 | 32-21 | 1 | 49,213 | Kevin Brown | Omar Olivares | Kevin Brown | Omar Olivares | Jeff Shaw | 252 | 261 | -9 |
| 1999-06-05 | vs ANA | 54 | W 7-4 | 33-21 | 1 | 44,779 | Chan Ho Park | Tim Belcher | Onan Masaoka | Tim Belcher | Jeff Shaw | 259 | 265 | -6 |
| 1999-06-06 | vs ANA | 55 | L 5-7 | 33-22 | 1 | 53,778 | Carlos Perez | Ken Hill | Ken Hill | Carlos Perez | Troy Percival | 264 | 272 | -8 |
| 1999-06-07 | vs TEX | 56 | L 2-3 | 33-23 | 1 | 26,462 | Ismael Valdez | Aaron Sele | Aaron Sele | Ismael Valdez | John Wetteland | 266 | 275 | -9 |
| 1999-06-08 | vs TEX | 57 | L 6-7 | 33-24 | 1 | 26,255 | Darren Dreifort | Mike Morgan | Jeff Zimmerman | Alan Mills | Mike Munoz | 272 | 282 | -10 |
| 1999-06-09 | vs TEX | 58 | W 7-2 | 34-24 | 1 | 46,539 | Kevin Brown | Mark Clark | Kevin Brown | Mark Clark | | 279 | 284 | -5 |
| 1999-06-11 | @ OAK | 59 | L 6-12 | 35-24 | 1 | 24,261 | Carlos Perez | Mike Oquist | Mike Oquist | Carlos Perez | T.J. Mathews | 285 | 296 | -11 |
| 1999-06-12 | @ OAK | 60 | L 3-4 | 35-25 | 1 | 31,391 | Ismael Valdez | Kenny Rogers | Kenny Rogers | Ismael Valdez | Billy Taylor | 288 | 300 | -12 |
| 1999-06-13 | @ OAK | 61 | L 3-9 | 35-26 | 1 | 27,973 | Darren Dreifort | Tim Hudson | Tim Hudson | Darren Dreifort | | 291 | 309 | -18 |
| 1999-06-15 | vs PIT | 62 | L 1-11 | 35-27 | 2 | 26,284 | Kevin Brown | Todd Ritchie | Todd Ritchie | Kevin Brown | | 292 | 320 | -28 |
| 1999-06-16 | vs PIT | 63 | W 6-5 | 36-27 | 1 | 25,384 | Carlos Perez | Francisco Cordova | Pedro Borbon | Brad Clontz | Jeff Shaw | 298 | 325 | -27 |
| 1999-06-17 | vs PIT | 64 | L 3-8 | 36-28 | 2 | 30,888 | Chan Ho Park | Kris Benson | Kris Benson | Chan Ho Park | | 301 | 333 | -32 |
| 1999-06-18 | vs PHI | 65 | L 1-2 | 36-29 | 2 | 41,590 | Ismael Valdez | Curt Schilling | Curt Schilling | Ismael Valdez | Wayne Gomes | 302 | 335 | -33 |
| 1999-06-19 | vs PHI | 66 | W 8-1 | 37-29 | 2 | 32,315 | Darren Dreifort | Robert Person | Darren Dreifort | Robert Person | | 310 | 336 | -26 |
| 1999-06-20 | vs PHI | 67 | W 3-2 | 38-29 | 2 | 46,347 | Kevin Brown | Chad Ogea | Kevin Brown | Chad Ogea | Jeff Shaw | 313 | 338 | -25 |
| 1999-06-22 | vs SDN | 68 | L 1-4 | 38-30 | 1 | 37,366 | Chan Ho Park | Sterling Hitchcock | Sterling Hitchcock | Chan Ho Park | Trevor Hoffman | 314 | 342 | -28 |
| 1999-06-23 | vs SDN | 69 | L 2-6 | 38-31 | 1 | 31,152 | Ismael Valdez | Woody Williams | Woody Williams | Ismael Valdez | Trevor Hoffman | 316 | 348 | -32 |
| 1999-06-24 | vs SDN | 70 | L 1-2 | 38-32 | 2 | 31,028 | Darren Dreifort | Andy Ashby | Andy Ashby | Darren Dreifort | Dan Miceli | 317 | 350 | -33 |
| 1999-06-25 | @ SFN | 71 | W 4-2 | 39-32 | 1 | 36,849 | Kevin Brown | Shawn Estes | Kevin Brown | Shawn Estes | Jeff Shaw | 321 | 352 | -31 |
| 1999-06-26 | @ SFN | 72 | W 7-6 | 40-32 | 1 | 44,766 | Carlos Perez | Chris Brock | Alan Mills | Robb Nen | Jeff Shaw | 328 | 358 | -30 |
| 1999-06-27 | @ SFN | 73 | L 7-8 | 40-33 | 1 | 42,530 | Chan Ho Park | Mark Gardner | Mark Gardner | Chan Ho Park | Robb Nen | 335 | 366 | -31 |
| 1999-06-29 | @ SDN | 74 | L 3-4 | 40-34 | 2 | 36,398 | Ismael Valdez | Andy Ashby | Donne Wall | Mike Maddux | | 338 | 370 | -32 |
| 1999-06-30 | @ SDN | 75 | L 2-11 | 41-34 | 2 | 44,965 | Kevin Brown | Brian Boehringer | Brian Boehringer | Kevin Brown | | 340 | 381 | -41 |
| 1999-07-01 | @ SDN | 76 | L 3-6 | 41-35 | 2 | 38,080 | Darren Dreifort | Matt Clement | Matt Clement | Darren Dreifort | Trevor Hoffman | 343 | 387 | -44 |
| 1999-07-02 | vs SFN | 77 | L 3-6 | 41-36 | 2 | 53,869 | Carlos Perez | Chris Brock | Chris Brock | Carlos Perez | Robb Nen | 346 | 393 | -47 |
| 1999-07-03 | vs SFN | 78 | L 1-9 | 41-37 | 2 | 41,770 | Chan Ho Park | Mark Gardner | Mark Gardner | Chan Ho Park | | 347 | 402 | -55 |
| 1999-07-04 | vs SFN | 79 | W 7-1 | 42-37 | 2 | 54,731 | Ismael Valdez | Kirk Rueter | Ismael Valdez | Kirk Rueter | | 354 | 403 | -49 |
| 1999-07-05 | @ COL | 80 | L 4-8 | 42-38 | 2 | 40,063 | Kevin Brown | Darryl Kile | Darryl Kile | Kevin Brown | | 358 | 411 | -53 |
| 1999-07-06 | @ COL | 81 | L 2-5 | 42-39 | 2 | 39,979 | Darren Dreifort | Pedro Astacio | Pedro Astacio | Darren Dreifort | | 360 | 416 | -56 |
| 1999-07-07 | @ COL | 82 | L 5-7 | 42-40 | 2 | 40,221 | Carlos Perez | Bobby Jones | Mike DeJean | Jamie Arnold | Dave Veres | 365 | 423 | -58 |
| 1999-07-08 | @ COL | 83 | W 11-8 | 42-41 | 3 | 42,024 | Chan Ho Park | Brian Bohanon | Chan Ho Park | Brian Bohanon | Jeff Shaw | 376 | 431 | -55 |
| 1999-07-09 | vs SEA | 84 | W 5-0 | 43-41 | 2 | 44,653 | Ismael Valdez | Freddy Garcia | Ismael Valdez | Freddy Garcia | | 381 | 431 | -50 |
| 1999-07-10 | vs SEA | 85 | W 2-1 | 44-41 | 2 | 50,813 | Kevin Brown | John Halama | Jeff Shaw | Jose Paniagua | | 383 | 432 | -49 |
| 1999-07-11 | vs SEA | 86 | W 14-3 | 44-42 | 2 | 43,211 | Darren Dreifort | Jeff Fassero | Darren Dreifort | Jeff Fassero | Onan Masaoka | 397 | 435 | -38 |
| 1999-07-15 | @ ANA | 87 | L 6-7 | 44-43 | 3 | 43,911 | Kevin Brown | Chuck Finley | Mark Petkovsek | Alan Mills | | 403 | 442 | -39 |
| 1999-07-16 | @ ANA | 88 | W 3-1 | 45-43 | 3 | 43,727 | Ismael Valdez | Omar Olivares | Ismael Valdez | Omar Olivares | Jeff Shaw | 406 | 443 | -37 |
| 1999-07-17 | @ ANA | 89 | W 13-3 | 45-44 | 3 | 39,808 | Chan Ho Park | Steve Sparks | Chan Ho Park | Steve Sparks | | 419 | 446 | -27 |
| 1999-07-18 | @ PIT | 90 | L 5-6 | 45-45 | 3 | 23,855 | Carlos Perez | Todd Ritchie | Scott Sauerbeck | Alan Mills | | 424 | 452 | -28 |
| 1999-07-19 | @ PIT | 91 | W 12-7 | 45-46 | 4 | 14,805 | Darren Dreifort | Jose Silva | Darren Dreifort | Jose Silva | | 436 | 459 | -23 |
| 1999-07-20 | @ PIT | 92 | W 8-4 | 46-46 | 4 | 16,921 | Kevin Brown | Jason Schmidt | Kevin Brown | Brad Clontz | | 444 | 463 | -19 |
| 1999-07-21 | vs COL | 93 | L 4-5 | 46-47 | 4 | 34,271 | Ismael Valdez | Pedro Astacio | Pedro Astacio | Ismael Valdez | Dave Veres | 448 | 468 | -20 |
| 1999-07-22 | vs COL | 94 | L 1-4 | 46-49 | 6 | 34,231 | Chan Ho Park | Bobby Jones | Bobby Jones | Chan Ho Park | Dave Veres | 449 | 472 | -23 |
| 1999-07-22 | vs COL | 95 | L 11-12 | 46-49 | 6 | 30,907 | Jamie Arnold | Brian Bohanon | David Lee | Onan Masaoka | Dave Veres | 460 | 484 | -24 |
| 1999-07-23 | @ ARI | 96 | L 1-10 | 46-50 | 4 | 43,031 | Carlos Perez | Omar Daal | Omar Daal | Carlos Perez | | 461 | 494 | -33 |
| 1999-07-24 | @ ARI | 97 | L 0-3 | 46-51 | 4 | 42,824 | Darren Dreifort | Brian Anderson | Brian Anderson | Darren Dreifort | Matt Mantei | 461 | 497 | -36 |
| 1999-07-25 | @ ARI | 98 | W 2-1 | 47-51 | 4 | 47,238 | Kevin Brown | Randy Johnson | Kevin Brown | Randy Johnson | Jeff Shaw | 463 | 498 | -35 |
| 1999-07-26 | vs CIN | 99 | L 3-5 | 47-52 | 4 | 28,477 | Ismael Valdez | Ron Villone | Stan Belinda | Jeff Shaw | | 466 | 503 | -37 |
| 1999-07-27 | vs CIN | 100 | L 3-5 | 47-53 | 4 | 36,619 | Chan Ho Park | Brett Tomko | Danny Graves | Alan Mills | Scott Williamson | 469 | 508 | -39 |
| 1999-07-28 | vs CIN | 101 | W 9-1 | 48-53 | 4 | 32,127 | Robinson Checo | Dennys Reyes | Robinson Checo | Dennys Reyes | Jamie Arnold | 478 | 509 | -31 |
| 1999-07-29 | vs CIN | 102 | L 5-7 | 48-54 | 4 | 32,758 | Darren Dreifort | Pete Harnisch | Pete Harnisch | Darren Dreifort | Scott Williamson | 483 | 516 | -33 |
| 1999-07-30 | vs ARI | 103 | L 5-6 | 48-55 | 4 | 45,839 | Kevin Brown | Brian Anderson | Bobby Chouinard | Jeff Shaw | Matt Mantei | 488 | 522 | -34 |
| 1999-07-31 | vs ARI | 104 | L 2-4 | 48-56 | 4 | 37,114 | Ismael Valdez | Randy Johnson | Randy Johnson | Ismael Valdez | | 490 | 526 | -36 |
| 1999-08-01 | vs ARI | 105 | W 4-2 | 49-56 | 4 | 46,991 | Chan Ho Park | Andy Benes | Onan Masaoka | Andy Benes | Jeff Shaw | 494 | 528 | -34 |
| 1999-08-03 | @ HOU | 106 | L 2-7 | 49-57 | 3 | 34,874 | Darren Dreifort | Mike Hampton | Mike Hampton | Darren Dreifort | | 496 | 535 | -39 |
| 1999-08-04 | @ HOU | 107 | W 2-1 | 50-57 | 3 | 31,771 | Kevin Brown | Chris Holt | Kevin Brown | Chris Holt | | 498 | 536 | -38 |
| 1999-08-05 | @ HOU | 108 | L 0-7 | 50-58 | 3 | 38,018 | Ismael Valdez | Shane Reynolds | Shane Reynolds | Ismael Valdez | | 498 | 543 | -45 |
| 1999-08-06 | @ NYN | 109 | L 1-2 | 50-59 | 3 | 43,825 | Chan Ho Park | Octavio Dotel | Octavio Dotel | Chan Ho Park | Armando Benitez | 499 | 545 | -46 |
| 1999-08-07 | @ NYN | 110 | W 7-6 | 51-59 | 3 | 53,656 | Jamie Arnold | Al Leiter | Pedro Borbon | Billy Taylor | Jeff Shaw | 506 | 551 | -45 |
| 1999-08-08 | @ NYN | 111 | W 14-3 | 51-60 | 3 | 39,803 | Darren Dreifort | Rick Reed | Darren Dreifort | Rick Reed | | 520 | 554 | -34 |
| 1999-08-09 | @ NYN | 112 | W 9-2 | 52-60 | 3 | 36,345 | Kevin Brown | Orel Hershiser | Kevin Brown | Orel Hershiser | | 529 | 556 | -27 |
| 1999-08-10 | @ MON | 113 | L 4-6 | 52-61 | 3 | 7,645 | Ismael Valdez | Mike Thurman | Mike Thurman | Ismael Valdez | Ugueth Urbina | 533 | 562 | -29 |
| 1999-08-11 | @ MON | 114 | W 9-7 | 53-61 | 3 | 8,756 | Chan Ho Park | Dan Smith | Mike Maddux | Bobby Ayala | Jeff Shaw | 542 | 569 | -27 |
| 1999-08-12 | @ MON | 115 | W 10-5 | 53-62 | 3 | 10,649 | Mike Judd | Dustin Hermanson | Mike Judd | Dustin Hermanson | | 552 | 574 | -22 |
| 1999-08-13 | vs ATL | 116 | L 3-7 | 53-63 | 5 | 40,363 | Darren Dreifort | Kevin Millwood | Kevin Millwood | Darren Dreifort | | 555 | 581 | -26 |
| 1999-08-14 | vs ATL | 117 | W 8-1 | 54-63 | 3 | 53,533 | Kevin Brown | John Smoltz | Kevin Brown | John Smoltz | | 563 | 582 | -19 |
| 1999-08-15 | vs ATL | 118 | L 4-5 | 54-64 | 5 | 41,606 | Ismael Valdez | Tom Glavine | Mike Remlinger | Jamie Arnold | John Rocker | 567 | 587 | -20 |
| 1999-08-16 | vs FLO | 119 | L 5-7 | 54-65 | 4 | 26,754 | Chan Ho Park | Vladimir Nunez | Vladimir Nunez | Chan Ho Park | | 572 | 594 | -22 |
| 1999-08-17 | vs FLO | 120 | L 1-6 | 54-66 | 4 | 30,354 | Mike Judd | A.J. Burnett | A.J. Burnett | Mike Judd | Dennis Springer | 573 | 600 | -27 |
| 1999-08-18 | vs FLO | 121 | W 7-0 | 55-66 | 4 | 36,463 | Darren Dreifort | Brian Meadows | Darren Dreifort | Brian Meadows | | 580 | 600 | -20 |
| 1999-08-20 | @ PHI | 122 | W 8-5 | 56-66 | 4 | 17,444 | Kevin Brown | Robert Person | Alan Mills | Wayne Gomes | | 588 | 605 | -17 |
| 1999-08-21 | @ PHI | 123 | L 5-6 | 56-67 | 4 | 22,078 | Ismael Valdez | Randy Wolf | Wayne Gomes | Onan Masaoka | | 593 | 611 | -18 |
| 1999-08-22 | @ PHI | 124 | W 9-7 | 57-67 | 4 | 22,510 | Chan Ho Park | Anthony Shumaker | Chan Ho Park | Anthony Shumaker | Jeff Shaw | 602 | 618 | -16 |
| 1999-08-23 | @ MIL | 125 | W 8-4 | 58-67 | 4 | 18,632 | Darren Dreifort | Hideo Nomo | Darren Dreifort | Hideo Nomo | Jeff Shaw | 610 | 622 | -12 |
| 1999-08-24 | @ MIL | 126 | W 5-2 | 59-67 | 4 | 21,828 | Mike Judd | Scott Karl | Mike Judd | Scott Karl | Jeff Shaw | 615 | 624 | -9 |
| 1999-08-25 | @ MIL | 127 | L 7-9 | 59-68 | 5 | 14,956 | Kevin Brown | Bill Pulsipher | Eric Plunk | Pedro Borbon | Bob Wickman | 622 | 633 | -11 |
| 1999-08-27 | vs CHN | 128 | W 9-0 | 60-68 | 4 | 44,230 | Ismael Valdez | Steve Trachsel | Ismael Valdez | Steve Trachsel | | 631 | 633 | -2 |
| 1999-08-28 | vs CHN | 129 | W 4-3 | 61-68 | 5 | 46,129 | Chan Ho Park | Andrew Lorraine | Chan Ho Park | Andrew Lorraine | Jeff Shaw | 635 | 636 | -1 |
| 1999-08-29 | vs CHN | 130 | L 0-6 | 61-69 | 4 | 47,411 | Darren Dreifort | Kyle Farnsworth | Kyle Farnsworth | Darren Dreifort | | 635 | 642 | -7 |
| 1999-08-30 | vs MIL | 131 | W 6-1 | 62-69 | 4 | 28,520 | Kevin Brown | Bill Pulsipher | Kevin Brown | Bill Pulsipher | | 641 | 643 | -2 |
| 1999-08-31 | vs MIL | 132 | W 5-3 | 63-69 | 4 | 32,771 | Mike Judd | Kyle Peterson | Mike Judd | Kyle Peterson | Jeff Shaw | 646 | 646 | 0 |
| 1999-09-01 | vs MIL | 133 | L 4-5 | 63-70 | 4 | 23,616 | Ismael Valdez | Cal Eldred | Cal Eldred | Ismael Valdez | Bob Wickman | 650 | 651 | -1 |
| 1999-09-03 | @ CHN | 134 | W 8-6 | 64-70 | 3 | 28,435 | Chan Ho Park | Andrew Lorraine | Chan Ho Park | Scott Sanders | Jeff Shaw | 658 | 657 | 1 |
| 1999-09-04 | @ CHN | 135 | W 6-0 | 65-70 | 3 | 39,048 | Kevin Brown | Kyle Farnsworth | Kevin Brown | Kyle Farnsworth | | 664 | 657 | 7 |
| 1999-09-05 | @ CHN | 136 | W 4-1 | 66-70 | 2 | 39,921 | Darren Dreifort | Jon Lieber | Darren Dreifort | Jon Lieber | Jeff Shaw | 668 | 658 | 10 |
| 1999-09-06 | @ FLO | 137 | L 6-8 | 66-71 | 3 | 12,089 | Ismael Valdez | Brian Meadows | Brian Meadows | Ismael Valdez | Antonio Alfonseca | 674 | 666 | 8 |
| 1999-09-07 | @ FLO | 138 | L 1-2 | 66-72 | 4 | 13,644 | Eric Gagne | Ryan Dempster | Jesus Sanchez | Matt Herges | Antonio Alfonseca | 675 | 668 | 7 |
| 1999-09-08 | @ FLO | 139 | L 4-5 | 66-73 | 4 | 9,615 | Chan Ho Park | Michael Tejera | Rafael Medina | Onan Masaoka | | 679 | 673 | 6 |
| 1999-09-09 | vs NYN | 140 | L 1-3 | 66-74 | 4 | 33,954 | Kevin Brown | Orel Hershiser | Orel Hershiser | Kevin Brown | Armando Benitez | 680 | 676 | 4 |
| 1999-09-10 | vs NYN | 141 | W 3-1 | 67-74 | 4 | 34,414 | Darren Dreifort | Al Leiter | Darren Dreifort | Al Leiter | Jeff Shaw | 683 | 677 | 6 |
| 1999-09-11 | vs NYN | 142 | L 2-6 | 67-75 | 4 | 47,747 | Ismael Valdez | Masato Yoshii | Masato Yoshii | Ismael Valdez | | 685 | 683 | 2 |
| 1999-09-12 | vs NYN | 143 | L 3-10 | 68-75 | 4 | 34,685 | Eric Gagne | Kenny Rogers | Kenny Rogers | Eric Gagne | | 688 | 693 | -5 |
| 1999-09-13 | vs MON | 144 | W 12-4 | 68-76 | 4 | 29,475 | Chan Ho Park | Dan Smith | Chan Ho Park | Dan Smith | | 700 | 697 | 3 |
| 1999-09-14 | vs MON | 145 | L 0-3 | 68-77 | 4 | 24,900 | Kevin Brown | Javier Vazquez | Javier Vazquez | Kevin Brown | | 700 | 700 | 0 |
| 1999-09-15 | vs MON | 146 | L 7-10 | 69-77 | 4 | 25,084 | Darren Dreifort | Jeremy Powell | Jeremy Powell | Jamie Arnold | Ugueth Urbina | 707 | 710 | -3 |
| 1999-09-17 | @ COL | 147 | L 10-18 | 69-78 | 4 | 44,170 | Ismael Valdez | Darryl Kile | Luther Hackman | Robinson Checo | | 717 | 728 | -11 |
| 1999-09-18 | @ COL | 148 | W 5-4 | 70-78 | 4 | 44,945 | Chan Ho Park | Pedro Astacio | Chan Ho Park | Pedro Astacio | Jeff Shaw | 722 | 732 | -10 |
| 1999-09-19 | @ COL | 149 | W 5-2 | 71-78 | 4 | 41,952 | Kevin Brown | John Thomson | Kevin Brown | John Thomson | Pedro Borbon | 727 | 734 | -7 |
| 1999-09-20 | vs SFN | 150 | W 6-5 | 72-78 | 4 | 33,280 | Eric Gagne | Russ Ortiz | Pedro Borbon | Alan Embree | | 733 | 739 | -6 |
| 1999-09-21 | vs SFN | 151 | W 9-4 | 73-78 | 3 | 31,881 | Jeff Williams | Kirk Rueter | Jeff Williams | Kirk Rueter | | 742 | 743 | -1 |
| 1999-09-22 | vs SFN | 152 | L 4-5 | 73-79 | 4 | 32,624 | Ismael Valdez | Joe Nathan | Mark Gardner | Pedro Borbon | Robb Nen | 746 | 748 | -2 |
| 1999-09-23 | vs SFN | 153 | W 5-3 | 74-79 | 3 | 34,589 | Chan Ho Park | Livan Hernandez | Chan Ho Park | Livan Hernandez | Jeff Shaw | 751 | 751 | 0 |
| 1999-09-24 | vs SDN | 154 | W 5-1 | 75-79 | 4 | 36,366 | Kevin Brown | Sterling Hitchcock | Kevin Brown | Sterling Hitchcock | | 756 | 752 | 4 |
| 1999-09-25 | vs SDN | 155 | L 2-3 | 75-80 | 4 | 41,067 | Eric Gagne | Woody Williams | Woody Williams | Matt Herges | Trevor Hoffman | 758 | 755 | 3 |
| 1999-09-26 | vs SDN | 156 | W 10-7 | 75-81 | 4 | 46,177 | Jeff Williams | Buddy Carlyle | Robinson Checo | Dan Miceli | | 768 | 762 | 6 |
| 1999-09-28 | @ SFN | 157 | W 6-3 | 76-81 | 4 | 34,786 | Chan Ho Park | Joe Nathan | Chan Ho Park | Joe Nathan | | 774 | 765 | 9 |
| 1999-09-29 | @ SFN | 158 | L 1-5 | 76-82 | 4 | 47,343 | Kevin Brown | Livan Hernandez | Livan Hernandez | Kevin Brown | Bronswell Patrick | 775 | 770 | 5 |
| 1999-09-30 | @ SFN | 159 | W 9-4 | 77-82 | 4 | 61,389 | Jeff Williams | Shawn Estes | Jeff Williams | Shawn Estes | | 784 | 774 | 10 |
| 1999-10-01 | @ HOU | 160 | W 5-1 | 78-82 | 4 | 50,791 | Eric Gagne | Shane Reynolds | Eric Gagne | Shane Reynolds | | 789 | 775 | 14 |
| 1999-10-02 | @ HOU | 161 | L 0-3 | 78-83 | 4 | 52,062 | Chan Ho Park | Jose Lima | Jose Lima | Chan Ho Park | Billy Wagner | 789 | 778 | 11 |
| 1999-10-03 | @ HOU | 162 | L 4-9 | 78-84 | 4 | 52,033 | Robinson Checo | Mike Hampton | Mike Hampton | Robinson Checo | | 793 | 787 | 6 |