| 1999 Winston Cup Race Winners | |||
| Race # | Race Location | Race | Winner |
| non-points | Daytona, FL | Bud Shootout | Mark Martin |
| 1 | Daytona, FL | Daytona 500 | Jeff Gordon |
| 2 | Rockingham, NC | Dura Lube/Big Kmart 400 | Mark Martin |
| 3 | Las Vegas, NV | Las Vegas 400 | Jeff Burton |
| 4 | Atlanta, GA | Cracker Barrel 400 | Jeff Gordon |
| 5 | Darlington, SC | TranSouth Financial 400 | Jeff Burton |
| 6 | Ft. Worth, TX | PrimeStar 500 | Terry Labonte |
| 7 | Bristol, TN | Food City 500 | Rusty Wallace |
| 8 | Martinsville, VA | Gppdy's Body Pain 500 | John Andretti |
| 9 | Talladega, AL | Diehard 500 | Dale Earnhardt |
| 10 | Fontana, CA | California 500 | Jeff Gordon |
| 11 | Richmond, VA | Pontiac Excitement 400 | Dale Jarrett |
| non-points | Concord, NC | The Winston | Terry Labonte |
| 12 | Concord, NC | Coca-Cola 600 | Jeff Burton |
| 13 | Dover, DE | MBNA Platinum 400 | Bobby Labonte |
| 14 | Michigan | Kmart 400 | Dale Jarrett |
| 15 | Ponoco, PA | Pocono 500 | Bobby Labonte |
| 16 | Sonoma, CA | Save Mart/Kragen 350 | Jeff Gordon |
| 17 | Daytona, FL | Pepsi 400 | Dale Jarrett |
| 18 | Louden, NH | Jiffy Lube 300 | Jeff Burton |
| 19 | Ponoco, PA | Pennsylvania 500 | Bobby Labonte |
| 20 | Indy,IN | Brickyard 400 | Dale Jarrett |
| 21 | Watkins Glen, NY | Frontier at The Glen | Jeff Gordon |
| 22 | Michigan | Pepsi 400 | Bobby Labonte |
| 23 | Bristol, TN | Goody's Headache Power 500 | Dale Earnhardt |
| 24 | Darlington, SC | Pepsi Southern 500 | Jeff Burton |
| 25 | Richmond, VA | Exide NASCAR Select Batteries 400 | Tony Stewart |
| 26 | Louden, NH | Dura-Lube/Kmart 500 | Joe Nemechek |
| 27 | Dover, DE | MBNA Gold 400 | Mark Martin |
| 28 | Martinsville, VA | NAPA Autocare 500 | Jeff Gordon |
| 29 | Concord, NC | UAW-GM Quality 500 | Jeff Gordon |
| 30 | Talladega, AL | Winston 500 | Dale Earnhardt |
| 31 | Rockingham, NC | Pop Secret Microwave Popcorn 400 | Jeff Burton |
| 32 | Phoenix, AZ | Checker Auto Parts/Dura Lube 500 | Tony Stewart |
| 33 | Homestead, Fl | Pennzoil 400 | Tony Stewart |
| 34 | Atlanta, GA | NAPA 500 | Bobby Labonte |