| 1 | 1999 | Daytona 500 | 20 | Joe Gibbs Racing | Toyota | Toyota | 2 | 28 |
| 2 | 1999 | Dura Lube / Big K 400 | 20 | Joe Gibbs Racing | Toyota | Toyota | 20 | 12 |
| 3 | 1999 | Las Vegas 400 | 20 | Joe Gibbs Racing | Toyota | Toyota | 20 | 36 |
| 4 | 1999 | Cracker Barrel 500 | 20 | Joe Gibbs Racing | Toyota | Toyota | 3 | 11 |
| 5 | 1999 | TranSouth Financial 400 | 20 | Joe Gibbs Racing | Toyota | Toyota | 10 | 6 |
| 6 | 1999 | Primestar 500 | 20 | Joe Gibbs Racing | Toyota | Toyota | 19 | 6 |
| 7 | 1999 | Food City 500 | 20 | Joe Gibbs Racing | Toyota | Toyota | 4 | 15 |
| 8 | 1999 | Goodys Body Pain 500 | 20 | Joe Gibbs Racing | Toyota | Toyota | 1 | 20 |
| 9 | 1999 | DieHard 500 | 20 | Joe Gibbs Racing | Toyota | Toyota | 8 | 5 |
| 10 | 1999 | California 500 Presented by NAPA | 20 | Joe Gibbs Racing | Toyota | Toyota | 7 | 4 |
| 11 | 1999 | Pontiac Excitement 400 | 20 | Joe Gibbs Racing | Toyota | Toyota | 30 | 15 |
| 12 | 1999 | Coca-Cola 600 | 20 | Joe Gibbs Racing | Toyota | Toyota | 27 | 4 |
| 13 | 1999 | MBNA Platinum 400 | 20 | Joe Gibbs Racing | Toyota | Toyota | 24 | 4 |
| 14 | 1999 | Kmart 400 Presented by Castrol Super Clean | 20 | Joe Gibbs Racing | Toyota | Toyota | 28 | 9 |
| 15 | 1999 | Pocono 500 | 20 | Joe Gibbs Racing | Toyota | Toyota | 12 | 6 |
| 16 | 1999 | Save Mart / Kragen 350 | 20 | Joe Gibbs Racing | Toyota | Toyota | 2 | 15 |
| 17 | 1999 | Pepsi 400 | 20 | Joe Gibbs Racing | Toyota | Toyota | 6 | 6 |
| 18 | 1999 | Jiffy Lube 300 | 20 | Joe Gibbs Racing | Toyota | Toyota | 10 | 10 |
| 19 | 1999 | Pennsylvania 500 | 20 | Joe Gibbs Racing | Toyota | Toyota | 12 | 4 |
| 20 | 1999 | Brickyard 400 | 20 | Joe Gibbs Racing | Toyota | Toyota | 11 | 7 |
| 21 | 1999 | Frontier @ the Glen | 20 | Joe Gibbs Racing | Toyota | Toyota | 4 | 6 |
| 22 | 1999 | Pepsi 400 Presented by Meijer | 20 | Joe Gibbs Racing | Toyota | Toyota | 37 | 3 |
| 23 | 1999 | Goodys Headache Powder 500 | 20 | Joe Gibbs Racing | Toyota | Toyota | 1 | 5 |
| 24 | 1999 | The 50th Pepsi Southern 500 | 20 | Joe Gibbs Racing | Toyota | Toyota | 19 | 12 |
| 25 | 1999 | Exide NASCAR Select Batteries 400 | 20 | Joe Gibbs Racing | Toyota | Toyota | 2 | 1 |
