
| 1999 NASCAR Winston Cup Driver Standings | ||||||||
| = Winston cup rookie year | ||||||||
| Average | Top | Top | ||||||
| Position | Driver | Points | Starts | Finish | Wins | 5's | 10's | Winnings |
| 1 | Jarrett, Dale | 5262 | 34 | 6.76 | 4 | 24 | 29 | $3,608,829 |
| 2 | Labonte, Bobby | 5061 | 34 | 9.06 | 5 | 23 | 26 | $3,550,341 |
| 3 | Martin, Mark | 4943 | 34 | 9.35 | 2 | 19 | 26 | $2,783,296 |
| 4 | Stewart, Tony | 4774 | 34 | 10.26 | 3 | 12 | 21 | $2,615,226 |
| 5 | Burton, Jeff | 4733 | 34 | 11.29 | 6 | 18 | 23 | $5,211,301 |
| 6 | Gordon, Jeff | 4620 | 34 | 12.91 | 7 | 18 | 21 | $5,281,361 |
| 7 | Earnhardt, Dale | 4492 | 34 | 12.03 | 3 | 7 | 21 | $2,712,089 |
| 8 | Wallace, Rusty | 4155 | 34 | 15.32 | 1 | 7 | 16 | $2,167,429 |
| 9 | Burton, Ward | 4062 | 34 | 16.09 | 0 | 6 | 16 | $2,115,824 |
| 10 | Skinner, Mike | 4003 | 34 | 16.62 | 0 | 5 | 14 | $2,222,321 |
| 11 | Mayfield, Jeremy | 3743 | 34 | 18.85 | 0 | 5 | 12 | $1,944,589 |
| 12 | Labonte, Terry | 3580 | 34 | 20.15 | 1 | 1 | 7 | $2,303,146 |
| 13 | Hamilton, Bobby | 3564 | 34 | 19.79 | 0 | 1 | 10 | $1,846,454 |
| 14 | Park, Steve | 3481 | 34 | 20.62 | 0 | 0 | 5 | $1,609,808 |
| 15 | Schrader, Ken | 3479 | 34 | 20.53 | 0 | 0 | 6 | $1,787,184 |
| 16 | Marlin, Sterling | 3397 | 34 | 21.74 | 0 | 2 | 5 | $1,651,371 |
| 17 | Andretti, John | 3394 | 34 | 22.06 | 1 | 3 | 10 | $1,861,706 |
| 18 | Dallenbach, Wally | 3367 | 34 | 21.74 | 0 | 1 | 6 | $1,604,968 |
| 19 | Irwin, Kenny | 3338 | 34 | 22.00 | 0 | 2 | 6 | $1,995,821 |
| 20 | Spencer, Jimmy | 3312 | 34 | 22.35 | 0 | 2 | 4 | $1,629,928 |
| 21 | Elliott, Bill | 3246 | 34 | 22.74 | 0 | 1 | 2 | $1,581,501 |
| 22 | Wallace, Kenny | 3210 | 34 | 23.26 | 0 | 3 | 5 | $1,376,708 |
| 23 | Little, Chad | 3193 | 34 | 23.35 | 0 | 0 | 5 | $1,585,976 |
| 24 | Sadler, Elliot | 3191 | 34 | 23.18 | 0 | 0 | 1 | $1,551,221 |
| 25 | Lepage, Kevin | 3185 | 34 | 23.29 | 0 | 1 | 2 | $1,552,841 |
| 26 | Petty, Kyle | 3103 | 32 | 22.53 | 0 | 0 | 9 | $1,278,953 |
| 27 | Bodine, Geoff | 3053 | 34 | 24.74 | 0 | 1 | 2 | $1,257,494 |
| 28 | Benson, Johnny | 3012 | 34 | 25.03 | 0 | 0 | 2 | $1,567,668 |
| 29 | Waltrip, Michael | 2974 | 34 | 25.56 | 0 | 1 | 3 | $1,701,160 |
| 30 | Nemechek, Joe | 2956 | 34 | 25.94 | 1 | 1 | 3 | $1,634,946 |
| 31 | Rudd, Ricky | 2922 | 34 | 26.18 | 0 | 3 | 5 | $1,632,011 |
| 32 | Mast, Rick | 2845 | 34 | 26.62 | 0 | 0 | 2 | $1,290,143 |
| 33 | Musgrave, Ted | 2689 | 32 | 26.50 | 0 | 0 | 2 | $1,162,403 |
| 34 | Nadeau, Jerry | 2686 | 34 | 28.15 | 0 | 1 | 2 | $1,370,229 |
| 35 | Bodine, Brett | 2351 | 32 | 30.00 | 0 | 0 | 0 | $1,321,396 |
| 36 | Green, David | 2320 | 32 | 30.22 | 0 | 0 | 0 | $1,079,536 |
| 37 | Waltrip, Darrell | 2158 | 27 | 27.81 | 0 | 0 | 0 | $973,133 |
| 38 | Bickle, Rich | 2149 | 24 | 24.63 | 0 | 0 | 2 | $892,456 |
| 39 | Pressley, Robert | 2050 | 28 | 30.11 | 0 | 0 | 0 | $1,033,223 |
| 40 | Irvan, Ernie | 1915 | 21 | 24.38 | 0 | 0 | 5 | $1,073,775 |
| 41 | Craven, Ricky | 1513 | 24 | 33.46 | 0 | 0 | 0 | $853,835 |
| 42 | Marcis, Dave | 1324 | 20 | 32.60 | 0 | 0 | 0 | $731,221 |
| 43 | Stricklin, Hut | 918 | 10 | 23.70 | 0 | 0 | 1 | $378,942 |
| 44 | Cope, Derrike | 915 | 15 | 34.00 | 0 | 0 | 0 | $617,976 |
| 45 | Jones, Buckshot | 676 | 10 | 31.80 | 0 | 0 | 0 | $345,128 |
| 46 | Bodine, Todd | 529 | 7 | 29.14 | 0 | 0 | 0 | $208,382 |
| 47 | Trickle, Dick | 528 | 9 | 34.78 | 0 | 0 | 0 | $275,364 |
| 48 | Earnhardt Jr, Dale | 500 | 5 | 21.40 | 0 | 0 | 1 | $162,095 |
| 49 | Kenseth, Matt | 434 | 5 | 26.00 | 0 | 1 | 1 | $143,561 |
| 50 | Grissom, Steve | 336 | 6 | 35.67 | 0 | 0 | 0 | $193,529 |
| 51 | Blaney, Dave | 332 | 5 | 32.20 | 0 | 0 | 0 | $212,170 |
| 52 | Berrier, Ed | 268 | 4 | 32.00 | 0 | 0 | 0 | $120,325 |
| 53 | Wallace, Mike | 185 | 2 | 23.50 | 0 | 0 | 0 | $135,261 |
| 54 | Fellows, Ron | 175 | 1 | 2.00 | 0 | 1 | 1 | $67,270 |
| 55 | Compton, Stacy | 174 | 3 | 35.00 | 0 | 0 | 0 | $92,600 |
| 56 | Hubert, Tom | 143 | 2 | 30.50 | 0 | 0 | 0 | $74,120 |
| 57 | Barrett, Stanton | 143 | 2 | 30.50 | 0 | 0 | 0 | $98,896 |
| 58 | Bliss, Mike | 104 | 2 | 37.00 | 0 | 0 | 0 | $42,475 |
| 59 | Said, Boris | 103 | 2 | 38.00 | 0 | 0 | 0 | $68,657 |
| 60 | Green, Jeff | 100 | 1 | 21.00 | 0 | 0 | 0 | $45,321 |
| 61 | LaJoie, Randy | 95 | 2 | 38.50 | 0 | 0 | 0 | $71,200 |
| 62 | Allen, Loy | 86 | 2 | 40.00 | 0 | 0 | 0 | $53,135 |
| 63 | Hornaday, Ron | 76 | 1 | 29.00 | 0 | 0 | 0 | $22,810 |
| 64 | Christopher, Ted | 70 | 1 | 31.00 | 0 | 0 | 0 | $22,360 |
| 65 | Shepard, Morgan | 67 | 1 | 32.00 | 0 | 0 | 0 | $69,303 |
| 66 | Bradberry, Gary | 58 | 1 | 35.00 | 0 | 0 | 0 | $48,189 |
| 67 | Murray, David | 46 | 1 | 39.00 | 0 | 0 | 0 | $21,965 |
| 68 | Gilliland, Butch | 34 | 1 | 43.00 | 0 | 0 | 0 | $25,415 |
| 69 | Hillenburg, Andy | 34 | 1 | 43.00 | 0 | 0 | 0 | $32,736 |
