| 1999-04-04 | @ SDN | 1 | W 8-2 | 1-0 | 1 | 27,104 | Darryl Kile | Andy Ashby | Darryl Kile | Andy Ashby | | 8 | 2 | 6 |
| 1999-04-06 | @ SDN | 2 | L 3-4 | 1-1 | 2 | 61,247 | Pedro Astacio | Sterling Hitchcock | Sterling Hitchcock | Pedro Astacio | Trevor Hoffman | 11 | 6 | 5 |
| 1999-04-07 | @ SDN | 3 | L 1-2 | 1-2 | 4 | 32,751 | Jamey Wright | Woody Williams | Roberto Rivera | Bobby Jones | | 12 | 8 | 4 |
| 1999-04-08 | @ LAN | 4 | W 4-2 | 2-2 | 3 | 27,879 | Brian Bohanon | Carlos Perez | Brian Bohanon | Carlos Perez | Dave Veres | 16 | 10 | 6 |
| 1999-04-09 | @ LAN | 5 | L 6-9 | 2-3 | 4 | 39,997 | John Thomson | Darren Dreifort | Darren Dreifort | John Thomson | Jeff Shaw | 22 | 19 | 3 |
| 1999-04-10 | @ LAN | 6 | L 0-2 | 2-4 | 4 | 44,503 | Darryl Kile | Kevin Brown | Kevin Brown | Darryl Kile | Jeff Shaw | 22 | 21 | 1 |
| 1999-04-12 | vs SDN | 7 | L 5-8 | 2-5 | 4 | 48,073 | Pedro Astacio | Woody Williams | Donne Wall | Dave Veres | Carlos Reyes | 27 | 29 | -2 |
| 1999-04-15 | vs SDN | 8 | W 6-4 | 3-5 | 4 | 40,027 | Brian Bohanon | Matt Clement | Brian Bohanon | Matt Clement | Dave Veres | 33 | 33 | 0 |
| 1999-04-17 | vs ATL | 9 | W 5-4 | 4-5 | 4 | 42,510 | Darryl Kile | Tom Glavine | Chuck McElroy | John Rocker | | 38 | 37 | 1 |
| 1999-04-18 | vs ATL | 10 | L 5-20 | 5-5 | 4 | 44,285 | Pedro Astacio | Greg Maddux | Greg Maddux | Pedro Astacio | | 43 | 57 | -14 |
| 1999-04-19 | vs MON | 11 | W 11-10 | 6-5 | 3 | 40,209 | Jamey Wright | Miguel Batista | Dave Veres | Ugueth Urbina | | 54 | 67 | -13 |
| 1999-04-22 | @ SFN | 12 | W 8-5 | 7-5 | 3 | 11,061 | Brian Bohanon | Kirk Rueter | Brian Bohanon | Kirk Rueter | Dave Veres | 62 | 72 | -10 |
| 1999-04-23 | @ SFN | 13 | L 2-7 | 7-6 | 4 | 16,271 | Darryl Kile | Russ Ortiz | Russ Ortiz | Darryl Kile | | 64 | 79 | -15 |
| 1999-04-24 | @ SFN | 14 | L 4-8 | 7-7 | 4 | 26,626 | Pedro Astacio | Shawn Estes | Shawn Estes | Pedro Astacio | | 68 | 87 | -19 |
| 1999-04-25 | @ SFN | 15 | L 6-7 | 7-8 | 4 | 23,099 | Jamey Wright | Chris Brock | Alan Embree | Mike DeJean | Robb Nen | 74 | 94 | -20 |
| 1999-04-27 | @ SLN | 16 | L 5-7 | 7-9 | 4 | 32,389 | John Thomson | Darren Oliver | Darren Oliver | John Thomson | Scott Radinsky | 79 | 101 | -22 |
| 1999-04-28 | @ SLN | 17 | W 9-7 | 8-9 | 4 | 34,545 | Brian Bohanon | Jose Jimenez | Brian Bohanon | Jose Jimenez | Dave Veres | 88 | 108 | -20 |
| 1999-04-29 | @ SLN | 18 | W 6-2 | 9-9 | 4 | 41,909 | Darryl Kile | Kent Mercker | Darryl Kile | Kent Mercker | | 94 | 110 | -16 |
| 1999-04-30 | @ PIT | 19 | W 7-2 | 10-9 | 3 | 17,466 | Pedro Astacio | Pete Schourek | Pedro Astacio | Pete Schourek | | 101 | 112 | -11 |
| 1999-05-01 | @ PIT | 20 | L 3-9 | 10-10 | 3 | 18,599 | Jamey Wright | Todd Ritchie | Todd Ritchie | Jamey Wright | | 104 | 121 | -17 |
| 1999-05-02 | @ PIT | 21 | L 5-8 | 10-11 | 3 | 19,215 | John Thomson | Jason Schmidt | Jason Schmidt | John Thomson | Mike Williams | 109 | 129 | -20 |
| 1999-05-03 | @ CHN | 22 | W 6-1 | 11-11 | 3 | 32,085 | Brian Bohanon | Steve Trachsel | Brian Bohanon | Steve Trachsel | | 115 | 130 | -15 |
| 1999-05-04 | @ CHN | 23 | L 12-13 | 11-12 | 3 | 28,888 | Darryl Kile | Kyle Farnsworth | Rod Beck | Jerry DiPoto | | 127 | 143 | -16 |
| 1999-05-05 | @ CHN | 24 | W 13-6 | 11-13 | 3 | 30,079 | Pedro Astacio | Terry Mulholland | Pedro Astacio | Terry Mulholland | | 140 | 149 | -9 |
| 1999-05-07 | vs PHI | 25 | L 1-8 | 11-14 | 4 | 41,465 | John Thomson | Curt Schilling | Curt Schilling | John Thomson | | 141 | 157 | -16 |
| 1999-05-08 | vs PHI | 26 | L 2-7 | 11-15 | 4 | 43,340 | Brian Bohanon | Joel Bennett | Joel Bennett | Brian Bohanon | | 143 | 164 | -21 |
| 1999-05-09 | vs PHI | 27 | L 8-10 | 12-15 | 4 | 40,251 | Darryl Kile | Chad Ogea | Ken Ryan | Dave Veres | Wayne Gomes | 151 | 174 | -23 |
| 1999-05-10 | vs NYN | 28 | W 10-3 | 12-16 | 4 | 40,021 | Pedro Astacio | Al Leiter | Pedro Astacio | Al Leiter | | 161 | 177 | -16 |
| 1999-05-11 | vs NYN | 29 | W 8-5 | 13-16 | 4 | 40,032 | Bobby Jones | Bobby Jones | Bobby Jones | Bobby Jones | | 169 | 182 | -13 |
| 1999-05-12 | vs NYN | 30 | L 5-10 | 14-16 | 4 | 41,011 | John Thomson | Rick Reed | Rick Reed | John Thomson | | 174 | 192 | -18 |
| 1999-05-14 | @ ARI | 31 | W 4-1 | 15-16 | 4 | 38,894 | Brian Bohanon | Andy Benes | Brian Bohanon | Andy Benes | | 178 | 193 | -15 |
| 1999-05-15 | @ ARI | 32 | L 2-9 | 15-17 | 4 | 40,853 | Darryl Kile | Randy Johnson | Randy Johnson | Darryl Kile | | 180 | 202 | -22 |
| 1999-05-16 | @ ARI | 33 | W 5-1 | 16-17 | 3 | 38,869 | Pedro Astacio | Omar Daal | Pedro Astacio | Omar Daal | | 185 | 203 | -18 |
| 1999-05-17 | vs CIN | 34 | L 2-7 | 16-18 | 4 | 40,067 | Bobby Jones | Pete Harnisch | Pete Harnisch | Bobby Jones | | 187 | 210 | -23 |
| 1999-05-18 | vs CIN | 35 | L 3-5 | 16-19 | 4 | 40,032 | Mark Brownson | Jason Bere | Danny Graves | Curt Leskanic | Scott Williamson | 190 | 215 | -25 |
| 1999-05-19 | vs CIN | 36 | L 12-24 | 16-20 | 4 | 41,044 | Brian Bohanon | Denny Neagle | Steve Parris | Jerry DiPoto | Ron Villone | 202 | 239 | -37 |
| 1999-05-20 | vs ARI | 37 | W 8-4 | 17-20 | 4 | 40,021 | Darryl Kile | Randy Johnson | Darryl Kile | Randy Johnson | | 210 | 243 | -33 |
| 1999-05-21 | vs ARI | 38 | W 8-7 | 18-20 | 4 | 44,205 | Pedro Astacio | Brian Anderson | Curt Leskanic | John Frascatore | | 218 | 250 | -32 |
| 1999-05-22 | vs ARI | 39 | L 3-8 | 18-21 | 4 | 48,594 | Bobby Jones | Omar Daal | Omar Daal | Bobby Jones | | 221 | 258 | -37 |
| 1999-05-23 | vs ARI | 40 | W 7-6 | 19-21 | 3 | 46,299 | Mark Brownson | Armando Reynoso | Chuck McElroy | Gregg Olson | | 228 | 264 | -36 |
| 1999-05-24 | @ HOU | 41 | L 2-5 | 19-22 | 3 | 20,772 | Brian Bohanon | Shane Reynolds | Shane Reynolds | Brian Bohanon | | 230 | 269 | -39 |
| 1999-05-25 | @ HOU | 42 | L 1-2 | 19-23 | 3 | 21,720 | Darryl Kile | Mike Hampton | Scott Elarton | Mike DeJean | | 231 | 271 | -40 |
| 1999-05-26 | @ HOU | 43 | L 2-3 | 19-24 | 3 | 24,476 | Pedro Astacio | Sean Bergman | Jay Powell | Pedro Astacio | | 233 | 274 | -41 |
| 1999-05-27 | @ HOU | 44 | W 4-3 | 20-24 | 3 | 25,146 | Bobby Jones | Chris Holt | Jerry DiPoto | Trever Miller | Dave Veres | 237 | 277 | -40 |
| 1999-05-28 | @ PHI | 45 | W 5-3 | 21-24 | 3 | 16,365 | Mark Brownson | Paul Byrd | Curt Leskanic | Paul Byrd | Dave Veres | 242 | 280 | -38 |
| 1999-05-29 | @ PHI | 46 | L 0-2 | 21-25 | 3 | 22,204 | Brian Bohanon | Curt Schilling | Curt Schilling | Brian Bohanon | | 242 | 282 | -40 |
| 1999-05-30 | @ PHI | 47 | W 1-0 | 22-25 | 3 | 30,358 | Darryl Kile | Chad Ogea | Darryl Kile | Jim Poole | Dave Veres | 243 | 282 | -39 |
| 1999-05-31 | @ ATL | 48 | L 1-3 | 22-26 | 4 | 34,136 | Pedro Astacio | Kevin Millwood | Kevin Millwood | Pedro Astacio | John Rocker | 244 | 285 | -41 |
| 1999-06-01 | @ ATL | 49 | L 2-7 | 22-27 | 4 | 30,297 | Bobby Jones | John Smoltz | John Smoltz | Bobby Jones | | 246 | 292 | -46 |
| 1999-06-02 | @ ATL | 50 | W 3-2 | 23-27 | 4 | 32,429 | Mark Brownson | Odalis Perez | Jerry DiPoto | Russ Springer | | 249 | 294 | -45 |
| 1999-06-04 | vs MIL | 51 | W 9-8 | 24-27 | 3 | 40,064 | Brian Bohanon | Jim Abbott | Dave Veres | Bob Wickman | | 258 | 302 | -44 |
| 1999-06-05 | vs MIL | 52 | W 12-11 | 25-27 | 3 | 43,409 | Darryl Kile | Hideo Nomo | Mike DeJean | Eric Plunk | Jerry DiPoto | 270 | 313 | -43 |
| 1999-06-06 | vs MIL | 53 | W 10-5 | 25-28 | 3 | 41,688 | Pedro Astacio | Scott Karl | Pedro Astacio | Scott Karl | | 280 | 318 | -38 |
| 1999-06-07 | vs SEA | 54 | L 2-4 | 25-29 | 3 | 40,692 | Bobby Jones | John Halama | John Halama | Bobby Jones | Jose Mesa | 282 | 322 | -40 |
| 1999-06-08 | vs SEA | 55 | L 5-10 | 26-29 | 3 | 41,940 | Mark Brownson | Frankie Rodriguez | Frankie Rodriguez | Mark Brownson | Ken Cloude | 287 | 332 | -45 |
| 1999-06-09 | vs SEA | 56 | W 16-11 | 27-29 | 3 | 40,671 | Brian Bohanon | Jeff Fassero | Brian Bohanon | Jeff Fassero | | 303 | 343 | -40 |
| 1999-06-11 | @ TEX | 57 | L 2-3 | 27-30 | 3 | 39,627 | Darryl Kile | Rick Helling | Jeff Zimmerman | Chuck McElroy | John Wetteland | 305 | 346 | -41 |
| 1999-06-12 | @ TEX | 58 | W 8-7 | 28-30 | 3 | 46,851 | Pedro Astacio | Aaron Sele | Pedro Astacio | Aaron Sele | Dave Veres | 313 | 353 | -40 |
| 1999-06-13 | @ TEX | 59 | W 4-2 | 29-30 | 3 | 39,651 | Bobby Jones | Mike Morgan | Bobby Jones | Mike Morgan | Dave Veres | 317 | 355 | -38 |
| 1999-06-14 | vs SFN | 60 | W 5-4 | 30-30 | 3 | 40,029 | Mark Brownson | Shawn Estes | Curt Leskanic | John Johnstone | Dave Veres | 322 | 359 | -37 |
| 1999-06-15 | vs SFN | 61 | W 15-6 | 30-31 | 3 | 40,037 | Brian Bohanon | Chris Brock | Brian Bohanon | Chris Brock | | 337 | 365 | -28 |
| 1999-06-16 | vs SFN | 62 | L 2-15 | 31-31 | 3 | 41,307 | Darryl Kile | Mark Gardner | Mark Gardner | Darryl Kile | | 339 | 380 | -41 |
| 1999-06-18 | vs FLO | 63 | W 11-10 | 32-31 | 3 | 46,394 | Pedro Astacio | Livan Hernandez | Chuck McElroy | Matt Mantei | | 350 | 390 | -40 |
| 1999-06-19 | vs FLO | 64 | W 10-2 | 32-32 | 3 | 47,051 | Bobby Jones | Alex Fernandez | Bobby Jones | Alex Fernandez | | 360 | 392 | -32 |
| 1999-06-20 | vs FLO | 65 | W 8-7 | 33-32 | 3 | 47,070 | Brian Bohanon | Ryan Dempster | Brian Bohanon | Ryan Dempster | Dave Veres | 368 | 399 | -31 |
| 1999-06-22 | vs CHN | 66 | L 12-13 | 33-33 | 3 | 48,081 | Darryl Kile | Steve Trachsel | Scott Sanders | Mike DeJean | Rick Aguilera | 380 | 412 | -32 |
| 1999-06-23 | vs CHN | 67 | W 10-1 | 34-33 | 3 | 48,189 | Pedro Astacio | Terry Mulholland | Pedro Astacio | Terry Mulholland | | 390 | 413 | -23 |
| 1999-06-24 | vs CHN | 68 | L 10-12 | 34-34 | 3 | 48,876 | Bobby Jones | Kevin Tapani | Kevin Tapani | Bobby Jones | | 400 | 425 | -25 |
| 1999-06-25 | @ SDN | 69 | L 1-10 | 34-35 | 3 | 22,362 | Brian Bohanon | Brian Boehringer | Brian Boehringer | Brian Bohanon | | 401 | 435 | -34 |
| 1999-06-26 | @ SDN | 70 | L 6-13 | 35-35 | 3 | 47,808 | Mark Brownson | Matt Clement | Matt Clement | Mark Brownson | | 407 | 448 | -41 |
| 1999-06-27 | @ SDN | 71 | L 3-5 | 35-36 | 3 | 25,177 | Darryl Kile | Sterling Hitchcock | Sterling Hitchcock | Darryl Kile | Trevor Hoffman | 410 | 453 | -43 |
| 1999-06-28 | @ SDN | 72 | L 7-8 | 35-37 | 3 | 41,107 | Pedro Astacio | Woody Williams | Woody Williams | Pedro Astacio | Trevor Hoffman | 417 | 461 | -44 |
| 1999-06-29 | @ SFN | 73 | L 1-10 | 35-38 | 4 | 11,490 | Bobby Jones | Kirk Rueter | Kirk Rueter | Bobby Jones | | 418 | 471 | -53 |
| 1999-06-30 | @ SFN | 74 | L 1-4 | 35-39 | 4 | 24,825 | Brian Bohanon | Russ Ortiz | Russ Ortiz | Brian Bohanon | Robb Nen | 419 | 475 | -56 |
| 1999-07-01 | @ SFN | 75 | L 1-7 | 35-40 | 4 | 23,172 | Darryl Kile | Shawn Estes | Shawn Estes | Darryl Kile | | 420 | 482 | -62 |
| 1999-07-02 | vs SDN | 76 | L 3-15 | 36-40 | 4 | 41,739 | Pedro Astacio | Sterling Hitchcock | Sterling Hitchcock | Pedro Astacio | | 423 | 497 | -74 |
| 1999-07-03 | vs SDN | 77 | W 12-10 | 37-40 | 4 | 38,375 | Roberto Ramirez | Woody Williams | Roberto Ramirez | Woody Williams | Dave Veres | 435 | 507 | -72 |
| 1999-07-03 | vs SDN | 78 | W 8-6 | 37-40 | 4 | 48,750 | Bobby Jones | Heath Murray | Bobby Jones | Heath Murray | Dave Veres | 443 | 513 | -70 |
| 1999-07-04 | vs SDN | 79 | L 0-11 | 38-41 | 3 | 38,059 | Brian Bohanon | Andy Ashby | Andy Ashby | Brian Bohanon | | 443 | 524 | -81 |
| 1999-07-05 | vs LAN | 80 | W 8-4 | 39-41 | 3 | 40,063 | Darryl Kile | Kevin Brown | Darryl Kile | Kevin Brown | | 451 | 528 | -77 |
| 1999-07-06 | vs LAN | 81 | W 5-2 | 40-41 | 3 | 39,979 | Pedro Astacio | Darren Dreifort | Pedro Astacio | Darren Dreifort | | 456 | 530 | -74 |
| 1999-07-07 | vs LAN | 82 | W 7-5 | 41-41 | 3 | 40,221 | Bobby Jones | Carlos Perez | Mike DeJean | Jamie Arnold | Dave Veres | 463 | 535 | -72 |
| 1999-07-08 | vs LAN | 83 | L 8-11 | 42-41 | 2 | 42,024 | Brian Bohanon | Chan Ho Park | Chan Ho Park | Brian Bohanon | Jeff Shaw | 471 | 546 | -75 |
| 1999-07-09 | vs ANA | 84 | L 6-9 | 42-42 | 3 | 44,122 | Darryl Kile | Chuck Finley | Chuck Finley | Darryl Kile | Troy Percival | 477 | 555 | -78 |
| 1999-07-10 | vs ANA | 85 | L 3-9 | 42-43 | 3 | 48,069 | Pedro Astacio | Omar Olivares | Omar Olivares | Pedro Astacio | | 480 | 564 | -84 |
| 1999-07-11 | vs ANA | 86 | W 8-2 | 43-43 | 3 | 42,585 | Bobby Jones | Mike Fyhrie | Jerry DiPoto | Mike Fyhrie | | 488 | 566 | -78 |
| 1999-07-15 | @ CIN | 87 | L 7-10 | 44-43 | 2 | 22,243 | Darryl Kile | Steve Parris | Steve Parris | Darryl Kile | Danny Graves | 495 | 576 | -81 |
| 1999-07-16 | @ CIN | 88 | W 6-2 | 45-43 | 2 | 29,552 | Pedro Astacio | Ron Villone | Pedro Astacio | Ron Villone | Dave Veres | 501 | 578 | -77 |
| 1999-07-17 | @ CIN | 89 | L 2-3 | 45-44 | 2 | 26,605 | Brian Bohanon | Brett Tomko | Scott Williamson | Jerry DiPoto | | 503 | 581 | -78 |
| 1999-07-18 | @ OAK | 90 | L 2-3 | 45-45 | 2 | 15,074 | Bobby Jones | Jimmy Haynes | Jimmy Haynes | Bobby Jones | Billy Taylor | 505 | 584 | -79 |
| 1999-07-19 | @ OAK | 91 | L 5-10 | 46-45 | 2 | 9,281 | Roberto Ramirez | Mike Oquist | Tim Worrell | Roberto Ramirez | Doug Jones | 510 | 594 | -84 |
| 1999-07-20 | @ OAK | 92 | L 3-4 | 46-46 | 3 | 13,414 | Darryl Kile | Kenny Rogers | Kenny Rogers | Darryl Kile | Billy Taylor | 513 | 598 | -85 |
| 1999-07-21 | @ LAN | 93 | W 5-4 | 47-46 | 3 | 34,271 | Pedro Astacio | Ismael Valdez | Pedro Astacio | Ismael Valdez | Dave Veres | 518 | 602 | -84 |
| 1999-07-22 | @ LAN | 94 | W 4-1 | 48-46 | 4 | 34,231 | Bobby Jones | Chan Ho Park | Bobby Jones | Chan Ho Park | Dave Veres | 522 | 603 | -81 |
| 1999-07-22 | @ LAN | 95 | W 12-11 | 48-46 | 4 | 30,907 | Brian Bohanon | Jamie Arnold | David Lee | Onan Masaoka | Dave Veres | 534 | 614 | -80 |
| 1999-07-23 | vs SLN | 96 | L 4-6 | 49-47 | 2 | 48,824 | Roberto Ramirez | Darren Oliver | Darren Oliver | Roberto Ramirez | Heathcliff Slocumb | 538 | 620 | -82 |
| 1999-07-24 | vs SLN | 97 | L 2-10 | 50-47 | 2 | 48,794 | Darryl Kile | Kent Mercker | Kent Mercker | Darryl Kile | | 540 | 630 | -90 |
| 1999-07-25 | vs SLN | 98 | L 4-6 | 50-48 | 2 | 48,845 | Pedro Astacio | Larry Luebbers | Larry Luebbers | Pedro Astacio | Manny Aybar | 544 | 636 | -92 |
| 1999-07-26 | vs HOU | 99 | L 5-8 | 50-49 | 2 | 42,740 | Bobby Jones | Scott Elarton | Brian Williams | Dave Veres | Billy Wagner | 549 | 644 | -95 |
| 1999-07-27 | vs HOU | 100 | L 3-6 | 50-50 | 2 | 41,952 | Brian Bohanon | Jose Lima | Jose Lima | Brian Bohanon | Billy Wagner | 552 | 650 | -98 |
| 1999-07-28 | vs HOU | 101 | L 8-16 | 51-50 | 2 | 43,201 | Roberto Ramirez | Mike Hampton | Mike Hampton | Roberto Ramirez | | 560 | 666 | -106 |
| 1999-07-29 | vs HOU | 102 | W 4-2 | 52-50 | 2 | 43,415 | Darryl Kile | Chris Holt | Darryl Kile | Chris Holt | Dave Veres | 564 | 668 | -104 |
| 1999-07-30 | @ SLN | 103 | W 5-4 | 53-50 | 2 | 46,208 | Pedro Astacio | Kent Mercker | Pedro Astacio | Manny Aybar | Dave Veres | 569 | 672 | -103 |
| 1999-07-31 | @ SLN | 104 | L 5-6 | 53-51 | 2 | 46,849 | Bobby Jones | Larry Luebbers | Lance Painter | Curt Leskanic | Ricky Bottalico | 574 | 678 | -104 |
| 1999-08-01 | @ SLN | 105 | W 5-4 | 54-51 | 2 | 45,906 | Brian Bohanon | Jose Jimenez | Brian Bohanon | Jose Jimenez | Dave Veres | 579 | 682 | -103 |
| 1999-08-03 | @ CIN | 106 | L 1-2 | 54-52 | 2 | 22,516 | Jamey Wright | Pete Harnisch | Scott Williamson | Mike DeJean | | 580 | 684 | -104 |
| 1999-08-04 | @ CIN | 107 | L 3-6 | 54-53 | 2 | 22,314 | Darryl Kile | Denny Neagle | Denny Neagle | Darryl Kile | Danny Graves | 583 | 690 | -107 |
| 1999-08-05 | @ CIN | 108 | W 2-1 | 55-53 | 2 | 24,318 | Pedro Astacio | Juan Guzman | Pedro Astacio | Juan Guzman | | 585 | 691 | -106 |
| 1999-08-06 | @ FLO | 109 | L 1-9 | 55-54 | 2 | 14,032 | Bobby Jones | Alex Fernandez | Alex Fernandez | Bobby Jones | | 586 | 700 | -114 |
| 1999-08-07 | @ FLO | 110 | L 1-4 | 55-55 | 2 | 18,469 | Brian Bohanon | Brian Meadows | Brian Meadows | Brian Bohanon | Antonio Alfonseca | 587 | 704 | -117 |
| 1999-08-08 | @ FLO | 111 | L 1-2 | 55-56 | 2 | 17,691 | Jamey Wright | Ryan Dempster | Ryan Dempster | Jamey Wright | Antonio Alfonseca | 588 | 706 | -118 |
| 1999-08-09 | @ MIL | 112 | L 6-7 | 55-57 | 2 | 17,463 | Darryl Kile | Bill Pulsipher | Bob Wickman | Dave Veres | | 594 | 713 | -119 |
| 1999-08-10 | @ MIL | 113 | L 1-2 | 55-58 | 2 | 19,758 | Pedro Astacio | Kyle Peterson | Rocky Coppinger | Dave Veres | | 595 | 715 | -120 |
| 1999-08-11 | @ MIL | 114 | W 8-5 | 56-58 | 2 | 21,632 | Bobby Jones | Steve Woodard | Bobby Jones | Steve Woodard | | 603 | 720 | -117 |
| 1999-08-13 | vs MON | 115 | L 13-14 | 56-60 | 3 | 40,092 | Jamey Wright | Mike Johnson | Ugueth Urbina | Jerry DiPoto | Anthony Telford | 616 | 734 | -118 |
| 1999-08-13 | vs MON | 116 | L 6-8 | 56-60 | 3 | 45,643 | Brian Bohanon | Javier Vazquez | Javier Vazquez | Brian Bohanon | Ugueth Urbina | 622 | 742 | -120 |
| 1999-08-14 | vs MON | 117 | W 11-8 | 56-61 | 2 | 46,739 | Darryl Kile | Jeremy Powell | Darryl Kile | Jeremy Powell | Dave Veres | 633 | 750 | -117 |
| 1999-08-15 | vs MON | 118 | W 8-2 | 57-62 | 3 | 43,702 | John Thomson | Mike Thurman | John Thomson | Mike Thurman | Roberto Ramirez | 641 | 752 | -111 |
| 1999-08-15 | vs MON | 119 | W 12-4 | 57-62 | 3 | 36,483 | Pedro Astacio | Shayne Bennett | Pedro Astacio | Shayne Bennett | | 653 | 756 | -103 |
| 1999-08-16 | vs ATL | 120 | L 6-14 | 58-62 | 2 | 47,519 | Bobby Jones | Greg Maddux | Greg Maddux | Bobby Jones | | 659 | 770 | -111 |
| 1999-08-17 | vs ATL | 121 | W 3-2 | 59-62 | 2 | 47,904 | Jamey Wright | Terry Mulholland | David Lee | Terry Mulholland | Dave Veres | 662 | 772 | -110 |
| 1999-08-18 | vs ATL | 122 | W 4-1 | 60-62 | 2 | 46,553 | Brian Bohanon | Kevin Millwood | Dave Veres | John Rocker | | 666 | 773 | -107 |
| 1999-08-19 | vs ATL | 123 | L 7-9 | 60-63 | 2 | 41,791 | Darryl Kile | John Smoltz | Bruce Chen | David Lee | Terry Mulholland | 673 | 782 | -109 |
| 1999-08-20 | @ CHN | 124 | W 11-3 | 60-64 | 2 | 40,130 | Pedro Astacio | Kyle Farnsworth | Pedro Astacio | Kyle Farnsworth | | 684 | 785 | -101 |
| 1999-08-21 | @ CHN | 125 | L 6-8 | 60-65 | 2 | 40,087 | John Thomson | Micah Bowie | Micah Bowie | John Thomson | Terry Adams | 690 | 793 | -103 |
| 1999-08-22 | @ CHN | 126 | W 3-2 | 61-65 | 2 | 38,424 | Jamey Wright | Steve Trachsel | Jamey Wright | Steve Trachsel | Dave Veres | 693 | 795 | -102 |
| 1999-08-24 | @ PIT | 127 | W 3-2 | 62-65 | 2 | 13,221 | Brian Bohanon | Kris Benson | Curt Leskanic | Mike Williams | Dave Veres | 696 | 797 | -101 |
| 1999-08-25 | @ PIT | 128 | L 3-9 | 62-66 | 3 | 12,535 | Darryl Kile | Chris Peters | Chris Peters | Darryl Kile | | 699 | 806 | -107 |
| 1999-08-26 | @ PIT | 129 | L 4-8 | 62-67 | 2 | 12,649 | Pedro Astacio | Jimmy Anderson | Jimmy Anderson | Pedro Astacio | | 703 | 814 | -111 |
| 1999-08-28 | vs PHI | 130 | W 11-6 | 62-68 | 4 | 42,744 | Jamey Wright | Chad Ogea | David Lee | Scott Aldred | | 714 | 820 | -106 |
| 1999-08-28 | vs PHI | 131 | W 4-0 | 62-68 | 4 | 47,217 | Brian Bohanon | Joe Grahe | Brian Bohanon | Joe Grahe | | 718 | 820 | -102 |
| 1999-08-29 | vs PHI | 132 | W 6-5 | 64-68 | 2 | 43,344 | Darryl Kile | Paul Byrd | Darryl Kile | Paul Byrd | Dave Veres | 724 | 825 | -101 |
| 1999-08-30 | vs PIT | 133 | L 8-11 | 65-68 | 2 | 41,872 | Pedro Astacio | Chris Peters | Chris Peters | Roberto Ramirez | Mike Williams | 732 | 836 | -104 |
| 1999-08-31 | vs PIT | 134 | L 8-9 | 65-69 | 2 | 41,729 | John Thomson | Jimmy Anderson | Mike Williams | David Lee | Jose Silva | 740 | 845 | -105 |
| 1999-09-01 | vs PIT | 135 | L 8-9 | 65-70 | 2 | 40,529 | Luther Hackman | Jason Schmidt | Scott Sauerbeck | Dave Veres | Brad Clontz | 748 | 854 | -106 |
| 1999-09-03 | @ NYN | 136 | W 5-2 | 66-70 | 2 | 36,102 | Jamey Wright | Orel Hershiser | Curt Leskanic | Turk Wendell | Dave Veres | 753 | 856 | -103 |
| 1999-09-04 | @ NYN | 137 | L 2-4 | 66-71 | 2 | 43,431 | Brian Bohanon | Al Leiter | Al Leiter | Brian Bohanon | Armando Benitez | 755 | 860 | -105 |
| 1999-09-05 | @ NYN | 138 | L 2-6 | 66-72 | 4 | 49,117 | Darryl Kile | Masato Yoshii | Masato Yoshii | Darryl Kile | | 757 | 866 | -109 |
| 1999-09-06 | @ MON | 139 | W 5-3 | 67-72 | 2 | 7,698 | Pedro Astacio | Mike Thurman | Pedro Astacio | Mike Thurman | Dave Veres | 762 | 869 | -107 |
| 1999-09-07 | @ MON | 140 | L 1-4 | 67-73 | 2 | 5,517 | John Thomson | Dustin Hermanson | Dustin Hermanson | John Thomson | Ugueth Urbina | 763 | 873 | -110 |
| 1999-09-08 | @ MON | 141 | W 5-1 | 68-73 | 2 | 5,548 | Jamey Wright | Dan Smith | Jamey Wright | Dan Smith | | 768 | 874 | -106 |
| 1999-09-10 | vs MIL | 142 | W 15-3 | 68-74 | 3 | 44,628 | Brian Bohanon | Bill Pulsipher | Brian Bohanon | Bill Pulsipher | | 783 | 877 | -94 |
| 1999-09-11 | vs MIL | 143 | W 7-6 | 69-74 | 3 | 44,566 | Darryl Kile | Steve Woodard | Jerry DiPoto | Rocky Coppinger | Dave Veres | 790 | 883 | -93 |
| 1999-09-12 | vs MIL | 144 | L 9-12 | 70-74 | 3 | 42,085 | Pedro Astacio | Jason Bere | Eric Plunk | Dave Veres | Bob Wickman | 799 | 895 | -96 |
| 1999-09-13 | vs NYN | 145 | L 5-6 | 70-75 | 3 | 40,547 | John Thomson | Rick Reed | Turk Wendell | Dave Veres | Armando Benitez | 804 | 901 | -97 |
| 1999-09-14 | vs NYN | 146 | W 7-2 | 71-75 | 3 | 41,090 | Jamey Wright | Octavio Dotel | Jamey Wright | Octavio Dotel | | 811 | 903 | -92 |
| 1999-09-15 | vs NYN | 147 | L 5-10 | 72-75 | 3 | 41,820 | Brian Bohanon | Orel Hershiser | Turk Wendell | Jerry DiPoto | Armando Benitez | 816 | 913 | -97 |
| 1999-09-17 | vs LAN | 148 | W 18-10 | 73-75 | 3 | 44,170 | Darryl Kile | Ismael Valdez | Luther Hackman | Robinson Checo | | 834 | 923 | -89 |
| 1999-09-18 | vs LAN | 149 | L 4-5 | 73-76 | 3 | 44,945 | Pedro Astacio | Chan Ho Park | Chan Ho Park | Pedro Astacio | Jeff Shaw | 838 | 928 | -90 |
| 1999-09-19 | vs LAN | 150 | L 2-5 | 73-77 | 3 | 41,952 | John Thomson | Kevin Brown | Kevin Brown | John Thomson | Pedro Borbon | 840 | 933 | -93 |
| 1999-09-20 | vs ARI | 151 | W 12-7 | 73-78 | 3 | 41,174 | Jamey Wright | Omar Daal | Jamey Wright | Omar Daal | | 852 | 940 | -88 |
| 1999-09-21 | vs ARI | 152 | L 6-7 | 73-79 | 4 | 41,559 | Brian Bohanon | Brian Anderson | Gregg Olson | Roberto Ramirez | Matt Mantei | 858 | 947 | -89 |
| 1999-09-22 | vs ARI | 153 | L 3-11 | 74-79 | 3 | 40,115 | Luther Hackman | Andy Benes | Andy Benes | Luther Hackman | | 861 | 958 | -97 |
| 1999-09-24 | @ FLO | 154 | W 5-3 | 75-79 | 3 | 18,941 | Pedro Astacio | Brian Meadows | Pedro Astacio | Brian Edmondson | Dave Veres | 866 | 961 | -95 |
| 1999-09-25 | @ FLO | 155 | L 2-8 | 75-80 | 3 | 27,271 | John Thomson | Ryan Dempster | Ryan Dempster | John Thomson | | 868 | 969 | -101 |
| 1999-09-26 | @ FLO | 156 | W 8-6 | 76-80 | 3 | 26,012 | Jamey Wright | Dennis Springer | Curt Leskanic | Rafael Medina | Dave Veres | 876 | 975 | -99 |
| 1999-09-27 | @ ARI | 157 | L 3-10 | 77-80 | 3 | 35,360 | Brian Bohanon | Brian Anderson | Brian Anderson | Brian Bohanon | | 879 | 985 | -106 |
| 1999-09-28 | @ ARI | 158 | L 3-9 | 77-81 | 3 | 31,447 | Luther Hackman | Andy Benes | Andy Benes | Luther Hackman | | 882 | 994 | -112 |
| 1999-09-29 | @ ARI | 159 | W 4-1 | 78-81 | 3 | 32,505 | Pedro Astacio | Armando Reynoso | Pedro Astacio | Armando Reynoso | | 886 | 995 | -109 |
| 1999-10-01 | vs SFN | 160 | L 4-9 | 78-82 | 3 | 41,302 | John Thomson | Russ Ortiz | Russ Ortiz | John Thomson | | 890 | 1004 | -114 |
| 1999-10-02 | vs SFN | 161 | L 7-16 | 79-82 | 3 | 38,393 | Jamey Wright | Kirk Rueter | Kirk Rueter | Jamey Wright | | 897 | 1020 | -123 |
| 1999-10-03 | vs SFN | 162 | W 9-8 | 80-82 | 3 | 40,117 | Brian Bohanon | Joe Nathan | Dave Veres | Alan Embree | | 906 | 1028 | -122 |