1999 W I N S T O N C U P® S C H E D U L E P A G E 1 (Pacific Standard Time)
| February | ||||||
| Date | Title Sponsor | Race Track | Radio | TV | Time | Race Winner |
| 7 | *Bud Shootout | Daytona International Speedway | MRN | CBS | 9 a.m. | Mark Martin |
| 11 | *Gatorade 125s | Daytona International Speedway | MRN | CBS** | 7 a.m. | 1st. Bobby Labonte
2nd. Dale Earnhardt |
| 14 | Daytona 500 | Daytona International Speedway | MRN | CBS | 9 a.m. | Jeff Gordon |
| 21 | North Carolina 400 | North Carolina Speedway | MRN | TNN | 9:30 a.m. | Mark Martin |
| March | ||||||
| Date | Title Sponsor | Race Track | Radio | TV | Time | Race Winner |
| 7 | Las Vegas 400 | Las Vegas Motor Speedway | MRN | ABC | 11:30 a.m. | Jeff Burton |
| 14 | Cracker Barrel 500 | Atlanta Motor Speedway | PRN | ABC | 10 a.m. | Jeff Gordon |
| 21 | TranSouth Financial 400 | Darlington Raceway | MRN | ESPN | 9:30 a.m. | Jeff Burton |
| 28 | PRIMESTAR 500 | Texas Motor Speedway | PRN | CBS | 11 a.m. | Terry Labonte |
| April | ||||||
| Date | Title Sponsor | Race Track | Radio | TV | Time | Race Winner |
| 11 | Food City 500 | Bristol Motor Speedway | PRN | ESPN | 10 a.m. | ?? |
| 18 | Goody's Body Pain 500 | Martinsville Speedway | MRN | ESPN | 10 a.m. | ?? |
| 25 | DieHard 500 | Talladega Superspeedway | MRN | ABC | 10 a.m. | ?? |
| May | ||||||
| Date | Title Sponsor | Race Track | Radio | TV | Time | Race Winner |
| 2 | California 500 presented by NAPA |
California Speedway | MRN | ABC | 11 a.m. | ?? |
| 15 | Pontiac Excitement 400 | Richmond International Raceway | MRN | ESPN | 4:30 p.m. | ?? |
| 22 | *The Winston | Charlotte Motor Speedway | MRN | TNN | 4:30 p.m. | ?? |
| 30 | Coca-Cola 600 | Charlotte Motor Speedway | PRN | TBS | 3:05 p.m. | ?? |
| June | ||||||
| Date | Title Sponsor | Race Track | Radio | TV | Time | Race Winner |
| 6 | MBNA Platinum 400 | Dover Downs International Speedway | MRN | TNN | 9:30 a.m. | ?? |
| 13 | Michigan 400 | Michigan Speedway | MRN | CBS | 10 a.m. | ?? |
| 20 | Pocono 500 | Pocono Raceway | MRN | TNN | 10 a.m. | ?? |
| 27 | Save Mart/Kragen 350K | Sears Point Raceway | PRN | ESPN | 1:30 p.m. | ?? |
| C O N T I N U E D O N P A G E 2 | ||||||
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