Count: 11
| Date | Series | Track | Race | Car Count | Winner | Start | Story |
| Friday, January 3, 2020 | WoOLM | Vado,NM | Battle at the Border Night 1 | 42 | Chris Madden | 2 | SMOKE IN THE DESERT: Madden Scores in Season Opener at Vado |
| Thursday, February 13, 2020 | WoOLM | Volusia,FL | DIRTcar Nationals | 51 | Jimmy Owens | 2 | FLORIDA’S NEWEST NIGHTMARE: Owens Earns First Career DIRTcar Nationals Gator Trophy |
| Saturday, February 15, 2020 | WoOLM | Volusia,FL | DIRTcar Nationals | 45 | Jimmy Owens | 2 | GATOR GETTERS: Owens Three-peats at Volusia, Sheppard Claims DIRTcar Nationals Title |
| Friday, March 6, 2020 | WoOLM | Duck River,TN | | 33 | Josh Richards | 2 | ROCKET MAN RETURNS: Richards Collects 77th Outlaws Win at Duck River |
| Friday, May 22, 2020 | WoOLM | Jackson,MN | | 26 | Ricky Weiss | 2 | OH CANADA! MANITOBA’S WEISS DOMINATES JACKSON |
| Saturday, June 20, 2020 | WoOLM | Volunteer,TN | | 29 | Zack Mitchell | 2 | KID QUICK: Zack Mitchell Beats Outlaws at Bulls Gap for First WoO Win |
| Saturday, July 18, 2020 | WoOLM | Red River Valley,ND | | 32 | Darrell Lanigan | 2 | BACK ON TOP: Lanigan Rides High Side to Red River Valley Victory |
| Sunday, July 19, 2020 | WoOLM | River Cities,ND | | 27 | Brandon Sheppard | 2 | PERFECT 10: SHEPPARD HITS DOUBLE DIGIT WINS IN RIVER CITIES ROUTE |
| Thursday, August 20, 2020 | WoOLM | Lincoln,PA | | 38 | Brandon Sheppard | 2 | DOMINANT DOZEN: Sheppard’s Reign Continues with 12th Win at Lincoln |
| Friday, August 21, 2020 | WoOLM | Williams Grove,PA | | 39 | Brandon Sheppard | 2 | KEYSTONE KING: Sheppard Outruns PA Posse at Williams Grove for 13th Win |
| Friday, September 25, 2020 | WoOLM | Thunder Mountain,PA | Eric Witherite Memorial | 37 | Scott Bloomquist | 2 | HE’S BACK: Scott Bloomquist is World of Outlaws Winner Again at Thunder Mountain |
