Legend:
| 3.1 Miles (5K) |
| 5 Miles |
| 6.2 Miles (10K) |
| 13.1 Miles (Half-marathon) |
| 26.2 Miles (Marathon) |
| Other |
| # | Race | Date | Location | Miles | Time | Pace | Place Overall | Division Place | Award | Conditions | Course Description | Previous Time |
| 1 | Race for the Cure | 5-9-99 | Pittsburgh, PA | 3.1 | 23:57 | 7:42 | 394/17,668 | 90/707 Men 20-29 | None | Very cool, overcast | Hilly /road | N/A |
| 2 | Charlotte’s Run | 5-15-99 | Beaver Falls, PA | 5 | 36:01 | 7:12 | 29/66 | 6/7 men 25-29 | None | Warm, sunny | Flat/road | N/A |
| 3 | Monroeville Classic | 5-23-99 | Monroeville, PA | 6.2 | 46:59 | 7:34 | 83/160 | 7/9 men 25-29 | None | Hot, overcast | Rolling/road | N/A |
| 4 | Lawyers Have Heart | 5-29-99 | Pittsburgh, PA | 3.1 | 22:01 | 7:06 | 20/63 | 8/17 men 26-35 | None | Warm, sunny | Rolling/Hilly road/cross country | N/A |
| 5 | June Fete | 6-6-99 | Abington, PA | 3.1 | 21:44 | 7:01 | 25/? | ? | None | Warm, sunny | Hilly/road | N/A |
| 6 | Covered Bridge | 6-12-99 | Washington, PA | 3.1 | 21:58 | 7:05 | 41/123 | 6th men 25–29 | None | Hot, sunny, humid | Gently rolling/ road | N/A |
| 7 | Donora Race of Champions | 6-19-99 | Donora, PA | 3.1 | 20:42 | 6:41 | 22/160 | 3/6 | 2nd Place division | Warm, sunny | Flat/ road | N/A |
| 8 | Butler Road Race | 6-26-99 | Butler, PA | 5 | 37:07 | 7:25 | 135/350 | 8/16 men 25–29 | None | Hot, sunny, humid | Rolling/road | N/A |
| 9 | Rolling Rock 5 Mile | 7-2-99 | Latrobe, PA | 5 | 35:24 | 7:08 | 82/? | 6/28 men 25-29 | None | Warm, sunny | Hilly/road | N/A |
| 10 | Whiskey Rebellion | 7-5-99 | Canonsburg, PA | 3.1 | 22:24 | 7:23 | 50/? | 2nd men 25-29 | 2nd Place division | VERY hot, sunny, humid | Rolling/road | N/A |
| 11 | Daily American | 7-10-99 | Somerset, PA | 6.2 | 45:08 | 7:16 | 41/290 | 4TH men 25-29 | None | Cool, humid, overcast | Rolling/hilly, road | N/A |
| 12 | Presque Isle Half-Marathon | 7-18-99 | Erie, PA | 13.1 | 1:42:44 | 7:51 | 84/289 | 10th men 25-29 | None | Hot, humid, clear | Flat/road | N/A |
| 13 | Thorn Hill 5K | 7-25-99 | Cranberry Twp, PA | 3.1 | 21:46 | 7:01 | 87/284 | 6/14 men 25-29 | None | Hot, clear | Rolling/ road | N/A |
| 14 | Turtle Trot 5K | 7-31-99 | Turtle Creek, PA | 3.1 | 21:08 | 6:49 | 74/308 | 5/9 men 25-29 | None | VERY hot, humid, clear | Mostly Flat/ road | N/A |
| 15 | Run for Moon Township | 8-7-99 | Moon Township, PA | 3.1 | 21:28 | 6:55 | 9/76 | 1/2 men 23-29 | 1st place division | Cool, clear | Hilly/ road | N/A |
| 16 | Links to Lake | 8-14-99 | Morgantown, WV | 3.1 | 20:59 | 6:46 | 68/261 | 3/10 men 25-29 | 3rd place division | Warm, very humid, clear | Rolling downhill, pt to pt/road | N/A |
| 17 | Edgewood 5K | 8-21-99 | Edgewood, PA | 3.1 | 21:34 | 6:57 | 38/211 | 5/15 men 25-29 | None | Cool, overcast | Hilly/road | N/A |
| 18 | Run Around the Square | 8-28-99 | Pittsburgh, PA | 3.1 | 21:18 | 6:52 | 96/1051 | 11/55 men 25-29 | None | Warm, clear, humid | Hilly/road/ cross country | N/A |
| 19 | ACS Labor Day Race | 9-6-99 | Washington, PA | 3.1 | 21:00 | 6:46 | 52/193 | 2/4 men 25-29 | 2nd place division | Hot, humid, partly cloudy | Downhill point to point/ road | N/A |
| 20 | IKEA-Montour Trail Half-Marathon | 9-11-99 | Pittsburgh, PA | 13.1 | 1:37:00 | 7:24 | 99/503 | 13/39 men 25-29 | None | Cool, clear, sunny | Flat/trail | N/A |
| 21 | Pace Setter 5K | 9-18-99 | Pittsburgh, PA | 3.1 | 20:38 | 6:39 | 4th out of 100 | 1st/10 Men 20-29 | 1st place division | Cool, clear sunny | Rolling/ cross-country | N/A |
| 22 | Baldwin Township Trot | 10-2-99 | Pittsburgh, PA | 3.1 | 21:24 | 6:54 | 15/113 | 2/7 Men 25-29 | 2nd place division | Cool, clear, sunny | Hilly/road | N/A |
| 23 | Ross Township 10K | 10-10-99 | Pittsburgh, PA | 6.2 | 45:35 | 7:20 | 12/55 | 4th Men 25-29 | 3rd place division | Cool-ish (~62º F), overcast, rain | Hilly/road | N/A |
| 24 | Great Presidents Road Race | 10-16-99 | Washington, PA | 3.1 | 20:36 | 6:39 | 8th out of 47 | 2nd Men 30-39 | 1st Alumni and 2nd division | Cool, sunny, clear | Hilly/road | N/A |
| 25 | Run Like Hell | 10-23-99 | Pittsburgh, PA | 3.1 | 20:59 | 6:46 | 80/708 | 10/59 men 30-34 | None | Cold, raining | Mostly flat | N/A |
| 26 | Pumpkin Chase | 10-30-99 | Wilmerding, PA | 3.1 | 21:21 | 6:53 | 71/225 | 4/6 Men 30-34 | 4th place division | Very cool, sunny, clear | Rolling/road | N/A |
| 27 | Chapel Challenge | 11-6-99 | Pittsburgh, PA | 6.2 | 44:08 | 7:06 | 14/78 | 3/12 Men 30-39 | 3rd place division | Cool, sunny, clear | Hilly/road | N/A |
| 28 | Race Against Tobacco | 11-13-99 | Pittsburgh, PA | 3.1 | 20:42 | 6:40 | 34/229 | 5/16 Men 30-34 | None | Cool, sunny, clear | Rolling/road | N/A |
| 29 | Pilgrim Prance | 11-20-99 | Mercer, PA | 6.2 | 43:18 | 6:59 | 51/125 | 4/6 Men 30-34 | None | Cool, partly cloudy | Rolling/road | N/A |
| 30 | Turkey Trot | 11-25-99 | Pittsburgh, PA | 5 | 33:30 | 6:42 | 125/1148 | 25/95 Men 30-34 | None | Cool, cloudy | Mostly flat/road/trail | N/A |
| 31 | Jingle Bell Run | 12-4-99 | Pittsburgh, PA | 3.1 | 21:12 | 6:50 | 50/609 | 6/34 Men 30-34 | None | Cool, sunny, clear | Hilly/road | N/A |
| 32 | Jingle Bell Run | 12-11-99 | Greensburg, PA | 3.1 | 20:21 | 6:33 | 23/210 | 3/30 Men 30-39 | 3rd place division | Cold, mostly sunny | Rolling/road | N/A |
| 33 | Rainbow Fun Run | 12-19-99 | Cleveland Heights, OH | ~4.5 | N/A | N/A | N/A | N/A | N/A | Cold (25º F), sunny | Mostly flat/road | N/A |
| 34 | Year-End Clearance Run | 12-26-99 | Uniontown, PA | 3.1 | 20:15 | 6:32 | 4th/21 | N/A | N/A | Cold (24º F) windy, overcast | Flat/road | N/A |
| 35 | Y2K 5K* | 12-31-99 | Pittsburgh, PA | ~3.0 | 19:11* | N/A | N/A | N/A | N/A | Cold (40º F) | Flat/road/paved trail | N/A |
* It was generally agreed that this course was short of the intended 3.1 mile distance