| DATE | WINNER | TRACK |
| February 13* | Dale Jarrett** | Daytona |
| February 17 (1)* | Bill Elliott | Daytona |
| February 17 (2)* | Ricky Rudd | Daytona |
| February 20 | Dale Jarrett | Daytona |
| February 27 | Bobby Labonte | Rockingham |
| March 5 | Jeff Burton | Las Vegas |
| March 12 | Dale Earnhardt Sr | Atlanta |
| March 19 | Ward Burton | Darlington |
| March 26 | Rusty Wallace | Bristol |
| April 2 | Dale Earnhardt Jr***! | Texas |
| April 9 | Mark Martin | Martinsville |
| April 16 | Jeff Gordon | Talladega |
| April 30 | Jeremy Mayfield | California |
| May 6 | Dale Earnhardt Jr*** | Richmond |
| May 20* | Dale Earnhardt Jr**** | Charlotte |
| May 28 | Matt Kenseth***! | Charlotte |
| June 4 | Tony Stewart | Dover |
| June 11 | Tony Stewart | Michigan |
| June 18 | Jeremy Mayfield | Pocono |
| June 25 | Jeff Gordon | Sears Point |
| July 1 | Jeff Burton | Daytona |
| July 9 | Tony Stewart | Louden† |
| July 23 | Rusty Wallace | Pocono |
| August 5 | Bobby Labonte | Indianapolis |
| August 13 | Steve Park!! | Watkins Glen |
| August 20 | Rusty Wallace | Michigan |
| August 26 | Rusty Wallace | Bristol |
| September 3 | Bobby Labonte | Darlington |
| September 9 | Jeff Gordon | Richmond |
| September 17 | Jeff Burton!!! | Louden |
| September 24 | Tony Stewart | Dover |
| October 1 | Tony Stewart | Martinsville |
| October 8 | Bobby Labonte | Charlotte |
| October 15 | Dale Earnhardt Sr | Talladega |
| October 22 | Dale Jarrett | Rockingham |
| November 5 | Jeff Burton | Phoenix |
| November 12!!!! | Tony Stewart | Homestead |
| November 21 | Jerry Nadeau!! | Atlanta |
** Dale Jarrett had to win the last chance qualifying race first. He then started the race in the 15th and final position...and was still able to win!
*** Rookie, Dale Earnhardt Jr is first repeat winner of 2000!
***! Race winner in rookie season!
**** Dale Earnhardt Jr is first rookie to ever win the Winston!
!! First ever Winston Cup win!
!!! Led every lap enroute to win!
!!!! Bobby Labonte clinches 2000 Winston Cup championship!
† Kenny Irwin killed in practice accident...7/7/2000!
| DATE | WINNER | TRACK |
| February 19 | Matt Kenseth | Daytona |
| February 26 | Mark Martin | Rockingham |
| March 4 | Jeff Burton | Las Vegas |
| March 11 | Mark Martin | Atlanta |
| March 18 | Mark Martin | Darlington |
| March 25 | Sterlin Marlin | Bristol |
| April 1 | Mark Martin | Texas |
| April 8 | Randy Lajoie | Nashville |
| April 15 | Joe Nemecheck | Talladega |
| April 29 | Matt Kenseth | California |
| May 5 | Jeff Green | Richmond |
| May 13 | Tim Fedewa | Louden NH† |
| May 27 | Jeff Burton | Charlotte |
| June 3 | Jason Keller | Dover |
| June 10 | Jeff Green | South Boston |
| June 17 | Jeff Green | Myrtle Beach |
| June 25 | Ron Fellows | Watkins Glen |
| July 2 | Jeff Green | Milwaukee |
| July 16 | Ron Hornaday | Nazareth |
| July 22 | Jeff Green | Pikes Peak |
| July 29 | Kevin Harvick | Gateway |
| August 4 | Ron Hornaday | Indy Raceway Park |
| August 19 | Todd Bodine | Michigan |
| August 25 | Kevin Harvick | Bristol |
| September 2 | Mark Martin | Darlington |
| September 8 | Jeff Burton | Richmond |
| September 23 | Matt Kenseth | Dover |
| October 7 | Matt Kenseth | Charlotte |
| October 21 | Jeff Green | Rockingham |
| October 29 | Kevin Harvick | Memphis* |
| November 4 | Jeff Burton | Phoenix |
| November 11 | Jeff Gordon | Homestead |
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