1999 NASCAR Winston Cup Winners
Winners
| Track | Winner |
| Daytona International Speedway | Jeff Gordon |
| Rockingham | Mark Martin |
| Las Vegas Motor Speedway* | Jeff Burton** |
| Atlanta Motor Speedway | Jeff Gordon |
| Darlington Raceway | Jeff Burton** |
| Texas Motor Speedway | Terry Labonte |
| Bristol Motor Speedway | Rusty Wallace |
| Martinsville Speedway | John Andretti |
| Talladega Superspeedway | Dale Earnhardt |
| California Speedway | Jeff Gordon |
| Richmond International Raceway | Dale Jarrett |
| Charlotte Motor Speedway(The Winston)*** | Terry Labonte |
| Charlotte Motor Speedway | Jeff Burton** |
| Dover Downs | Bobby Labonte |
| Michigan Speedway | Dale Jarrett |
| Pocono Raceway | Bobby Labonte |
| Sears Point Raceway | Jeff Gordon |
| Daytona International Speedway | Dale Jarrett |
| Loudon | Jeff Burton** |
| Pocono Raceway | Bobby Labonte |
| Indianapolis Motor Speedway | Dale Jarrett |
| Watkins Glen International | Jeff Gordon |
| Michigan Speedway | Bobby Labonte |
| Bristol Motor Speedway | Dale Earnhardt |
| Darlington Raceway | Jeff Burton** |
| Richmond International Raceway | Tony Stewart |
| Loudon | Joe Nemechek |
| Dover Downs | Mark Martin |
| Martinsville Speedway | Jeff Gordon |
| Charlotte Motor Speedway | Jeff Gordon |
| Talladega Superspeedway | Dale Earnhardt |
| Rockingham | Jeff Burton** |
| Phoenix International Raceway | Tony Stewart |
| Homestead-Miami Speedway | Tony Stewart |
| Atlanta Motor Speedway | Bobby Labonte |
*I was there
** Jeff Burton is the best
*** Non-points race
Season Wins List
| Driver | Wins |
| Jeff Gordon | 7 |
| Jeff Burton | 6 |
| Bobby Labonte | 5 |
| Dale Jarrett | 4 |
| Dale Earnhardt | 3 |
| Tony Stewart | 3 |
| Mark Martin | 2 |
| John Andretti | 1 |
| Terry Labonte | 1 |
| Joe Nemechek | 1 |
| Rusty Wallace | 1 |
Final Point Standings
| Driver | Points |
| Dale Jarrett | 5262 |
| Bobby Labonte | 5061 |
| Mark Martin | 4943 |
| Tony Stewart | 4774 |
| Jeff Burton | 4733 |