Clevite Engine Builder of the
Year
Doug Yates
$50,000
Plasti-Kote Quality Finish
Award
Todd Parrot
$50,000
DuPont Point Fund
Award
Dale Jarrett
$50,000
Goodyear Tire Award
Dale
Jarrett
$35,000
Tosco Gasoline Contingency Award
Dale Jarrett
$50,000
| RACE | LAPS | START | FINISH | MONEY | PTS | RANK |
| Daytona 500 | 200 | 8 | 37 | $146,879 | 57 | 36 |
| Dura Lube 400 | 393 | 11 | 2 | $ 83,675 | 170 | 13 |
| Las Vegas 400 | 267 | 9 | 11 | $ 85,240 | 130 | 11 |
| Cracker Barrel 500 | 325 | 4 | 5 | $ 53,675 | 155 | 6 |
| TranSouth 400 | 164 | 21 | 4 | $ 60,305 | 160 | 6 |
| Primestar 500 | 334 | 12 | 2 | $250,100 | 175 | 3 |
| Food City 500 | 500 | 16 | 3 | $ 68,650 | 165 | 2 |
| Goody's 500 | 500 | 31 | 8 | $ 46,825 | 142 | 2 |
| DieHard 500 | 188 | 23 | 2 | $104,955 | 175 | 2 |
| California 500 | 250 | 2 | 5 | $ 71,140 | 160 | 2 |
| Pontiac 400 | 400 | 21 | 1 | $169,715 | 180 | 1 |
| *The Winston | 70 | 6 | 19 | $ 18,000 | 0 | 1 |
| Coca-Cola 600 | 400 | 28 | 5 | $ 81,125 | 155 | 1 |
| MBNA Platinum 400 | 400 | 2 | 5 | $ 67,745 | 160 | 1 |
| KMart 400 | 200 | 6 | 1 | $151,240 | 185 | 1 |
| Pocono 500 | 200 | 2 | 3 | $ 86,670 | 175 | 1 |
| Kragen 350 | 112 | 29 | 6 | $ 53,940 | 150 | 1 |
| Pepsi 400 | 160 | 12 | 1 | $164,965 | 180 | 1 |
| Jiffy Lube 300 | 300 | 9 | 4 | $ 75,550 | 165 | 1 |
| Pennsylvania 500 | 200 | 15 | 2 | $ 95,695 | 175 | 1 |
| Brickyard 400 | 160 | 4 | 1 | $712,240 | 185 | 1 |
| Frontier at The Glen | 90 | 9 | 4 | $ 59,900 | 160 | 1 |
| Pepsi 400 | 200 | 3 | 4 | $ 57,650 | 165 | 1 |
| Goody's Powder 500 | 500 | 25 | 38 | $ 43,425 | 49 | 1 |
| Southern 500 | 270 | 36 | 16 | $ 50,960 | 120 | 1 |
| Exide 400 | 400 | 13 | 3 | $ 64,605 | 165 | 1 |
| Dura-Lube 300 | 300 | 2 | 18 | $ 66,500 | 114 | 1 |
| MBNA Gold 400 | 400 | 26 | 3 | $ 74,935 | 170 | 1 |
| NAPA AutoCare 500 | 500 | 14 | 10 | $ 52,790 | 134 | 1 |
| UAW-GM 500 | 334 | 9 | 7 | $ 65,475 | 151 | 1 |
| Winston 500 | 188 | 17 | 2 | $ 85,345 | 175 | 1 |
| Popcorn 400 | 393 | 3 | 4 | $ 61,175 | 170 | 1 |
| Dura Lube 500 | 312 | 5 | 6 | $ 82,475 | 155 | 1 |
| **Pennzoil 400 | 267 | 12 | 5 | $100,865 | 160 | 1 |
| NAPA 500 | 325 | 10 | 2 | $ 94,400 | 175 | 1 |
| **Clinched 1999 Winston Cup championship | ||||||
| *non-points event | ||||||