Count: 12
| Date | Series | Track | Race | Car Count | Winner | Start | Story |
| Friday, February 8, 2019 | WoO | Volusia,FL | DIRTcar Nationals | 33 | Daryn Pittman | 3 | Pittman Powers to Opening Night Victory at Volusia Speedway Park’s DIRTcar Nationals |
| Saturday, February 9, 2019 | WoO | Volusia,FL | DIRTcar Nationals | 31 | Daryn Pittman | 3 | Pittman Goes Two-for-Two at Volusia Speedway Park’s DIRTcar Nationals |
| Saturday, March 16, 2019 | WoO | Stockton,CA | Western Spring Shootout | 35 | Logan Schuchart | 1 | Schuchart bucks wild Stockton to become sixth different winner in seven races |
| Friday, May 17, 2019 | WoO | Williams Grove,PA | | 40 | David Gravel | 1 | David Gravel rides low line to Morgan Cup first round win |
| Friday, May 31, 2019 | WoO | Nashville,TN | Music City Outlaw Nationals | 40 | Donny Schatz | 3 | Schatz makes late race pass on Bill Balog to be first World of Outlaws winner in Nashville |
| Saturday, June 1, 2019 | WoO | Nashville,TN | Music City Outlaw Nationals | 37 | Shane Stewart | 2 | Shane Stewart beats Brent Marks for Music City Outlaw Nationals win in thrilling show |
| Thursday, June 27, 2019 | WoO | Jackson,MN | Jackson Nationals Prelim | 42 | Brad Sweet | 6 | Brad Sweet makes late race pass on David Gravel to claim third win in-a-row, 40th overall |
| Wednesday, July 3, 2019 | WoO | Brown County,SD | | 22 | Brad Sweet | 5 | Brad Sweet takes advantage of Logan Schuchart’s mistake to get eighth win of the season at Brown County Speedway |
| Saturday, July 13, 2019 | WoO | Wilmot,WI | Badger 40 | 23 | Donny Schatz | 1 | RETURN TO FORM: Donny Schatz dominates at Wilmot Raceway |
| Monday, September 2, 2019 | WoO | Grays Harbor,WA | | 17 | Daryn Pittman | 2 | LABORING VICTORY: Daryn Pittman wins Labor Day race at Grays Harbor Raceway |
| Wednesday, September 25, 2019 | WoO | Jacksonville,IL | | 36 | Carson Macedo | 2 | Carson Macedo wins thrilling show at Jacksonville Speedway |
| Saturday, September 28, 2019 | WoO | Lernerville,PA | Commonwealth Clash | 32 | Brad Sweet | 1 | Brad Sweet earns his 50th career win, extends points lead at Lernerville |
