| 1 | 1999 | Kmart 400 Presented by Castrol Super Clean | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 10 | 6 |
| 2 | 1999 | Pennsylvania 500 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 32 | 8 |
| 3 | 1999 | The 50th Pepsi Southern 500 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 39 | 10 |
| 4 | 1999 | MBNA Gold 400 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 10 | 9 |
| 5 | 1999 | UAW-GM Quality 500 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 14 | 10 |
| 6 | 2000 | Dura Lube / Kmart 400 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 18 | 9 |
| 7 | 2000 | Cracker Barrel Old Country Store 500 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 3 | 4 |
| 8 | 2000 | Food City 500 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 1 | 7 |
| 9 | 2000 | Coca-Cola 600 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 18 | 9 |
| 10 | 2000 | Global Crossing @ The Glen | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 18 | 1 |
| 11 | 2000 | goracing.com 500 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 3 | 5 |
| 12 | 2000 | Pepsi Southern 500 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 39 | 10 |
| 13 | 2000 | Chevrolet Monte Carlo 400 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 12 | 4 |
| 14 | 2000 | MBNA.com 400 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 28 | 4 |
| 15 | 2000 | UAW-GM Quality 500 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 39 | 7 |
| 16 | 2000 | Pop Secret Microwave Popcorn 400 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 17 | 6 |
| 17 | 2000 | Checker Auto Parts / Dura Lube 500k | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 5 | 3 |
| 18 | 2000 | Pennzoil 400 Presented by Discount Auto Parts | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 1 | 8 |
| 19 | 2001 | Dura Lube 400 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 2 | 1 |
| 20 | 2001 | UAW-Daimler Chrysler 400 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 21 | 7 |
| 21 | 2001 | Carolina Dodge Dealers 400 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 13 | 2 |
| 22 | 2001 | Food City 500 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 17 | 9 |
| 23 | 2001 | Harrahs 500 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 5 | 2 |
| 24 | 2001 | Pontiac Excitement 400 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 4 | 4 |
| 25 | 2001 | MBNA Platinum 400 | 1 | Dale Earnhardt, Inc. | Chevrolet | Chevrolet | 9 | 2 |
