| Stewart's 1999 Totals | Starts | Avg.Start | Provisionals | Avg.Finish | Points | Finished | Winnings | |
| 34 | 12.6 | 2 | 10.2 | 4774 | 4th | $2,451,939 | ||
| No. | Race | Start | Finish | Points | Standing Pos. | Winnings | Status | |
| 1 | Daytona 500 | 2 | 28 | 79 | 28 | $102,204 | Running | |
| 2 | Dura-Lube/Big Kmart 400 | 20 | 12 | 127 | 18 | $36,785 | Running | |
| 3 | Las Vegas 400 | 20 | 36 | 55 | 26 | $46,200 | Running | |
| 4 | Cracker Barrel 500 | 3 | 11 | 135 | 19 | $35,815 | Running | |
| 5 | TranSouth Financial 500 | 10 | 6 | 150 | 15 | $44,240 | Running | |
| 6 | PRIMESTAR 500 | 19 | 6 | 150 | 13 | $107,315 | Running | |
| 7 | Ford City 500 | 4 | 15 | 123 | 12 | $48,505 | Running | |
| 8 | Goody's Body Pain 500 | 1 | 20 | 103 | 10 | $33,615 | Running | |
| 9 | DieHard 500 | 8 | 5 | 160 | 7 | $59,855 | Running | |
| 10 | California 500 | 7 | 4 | 165 | 6 | $68,175 | Running | |
| 11 | Pontiac Excitement 400 | 30 | 15 | 118 | 7 | $27,225 | Running | |
| 12 | Coca-Cola 600 | 27 | 4 | 165 | 5 | $76,275 | Running | |
| 13 | MBNA Platinum 400 | 24 | 4 | 170 | 5 | $63,205 | Running | |
| 14 | Kmart 400 | 28 | 9 | 138 | 5 | $34,450 | Gas | |
| 15 | Pocono 500 | 12 | 6 | 155 | 6 | $53,255 | Running | |
| 16 | Save Mart/Kragen 350 | 2 | 15 | 118 | 6 | $35,965 | Running | |
| 17 | Pepsi 400 | 6 | 6 | 150 | 6 | $52,475 | Running | |
| 18 | Jiffy Lube 300 | 10 | 10 | 144 | 6 | $55,715 | Running | |
| 19 | Pennsylvania 500 | 12 | 4 | 160 | 5 | $70,970 | Running | |
| 20 | Brickyard 400 | 11 | 7 | 146 | 5 | $162,635 | Running | |
| 21 | Frontier @ The Glen | 4 | 6 | 150 | 6 | $45,240 | Running | |
| 22 | Pepsi 400 | 37 | 3 | 170 | 5 | $60,505 | Running | |
| 23 | Goody's Headache Powder 500 | 1 | 5 | 165 | 5 | $64,915 | Running | |
| 24 | Pepsi Southern 500 | 19 | 12 | 127 | 5 | $46,620 | Running | |
| 25 | Exide Batteries 400 | 2 | 1 | 185 | 4 | $135,160 | Running | |
| 26 | Dura Lube/Kmart 300 | 5 | 2 | 175 | 4 | $114,790 | Running | |
| 27 | MBNA Gold 400 | 3 | 2 | 175 | 4 | $88,875 | Running | |
| 28 | NAPA AutoCare 500 | 37 | 41 | 40 | 4 | $34,600 | Running | |
| 29 | UAW-GM Quality 500 | 5 | 19 | 106 | 5 | $39,315 | Running | |
| 30 | Winston 500 | 5 | 6 | 155 | 5 | $60,875 | Running | |
| 31 | Pop Secret 400 | 8 | 12 | 127 | 5 | $43,600 | Running | |
| 32 | Checker Auto Parts/Dura Lube 500 | 11 | 1 | 185 | 4 | $168,485 | Running | |
| 33 | Pennzoil 400 | 7 | 1 | 180 | 4 | $278,265 | Running | |
| 34 | NAPA 500 | 30 | 15 | 123 | 4 | $55,815 | Running | |