Count: 18
| Date | Series | Track | Race | Car Count | Winner | Story |
| Friday, April 26, 2019 | WoO | Lake Ozark,MO | | 32 | Brad Sweet | Brad Sweet passes David Gravel in closing laps to win at Lake Ozark |
| Wednesday, May 15, 2019 | WoO | Lincoln,PA | Gettysburg Clash | 43 | Lance DeWease | Lance Dewease out duels World of Outlaws for PA Posse victory in Abbottstown |
| Friday, May 24, 2019 | WoO | Charlotte,NC | Patriot Nationals | 31 | Gio Scelzi | Giovanni Scelzi beats NASCAR’s Kyle Larson to win first night of the United Rentals Patriot Nationals in Charlotte |
| Monday, May 27, 2019 | WoO | Lawrenceburg,IN | | 31 | Kyle Larson | NASCAR’s Kyle Larson claims World of Outlaws win at Lawrenceburg Speedway after intense battle with Christopher Bell |
| Saturday, June 1, 2019 | WoO | Nashville,TN | Music City Outlaw Nationals | 37 | Shane Stewart | Shane Stewart beats Brent Marks for Music City Outlaw Nationals win in thrilling show |
| Saturday, June 8, 2019 | WoO | Granite City,MN | | 24 | Brad Sweet | Brad Sweet overcomes mistake to win big at Granite City Speedway |
| Saturday, June 15, 2019 | WoO | Knoxville,IA | | 38 | Brad Sweet | Brad Sweet wins second night of World of Outlaws doubleheader weekend at Knoxville Raceway |
| Saturday, June 22, 2019 | WoO | Beaver Dam,WI | Jim "JB" Boyd Memorial | 27 | Brad Sweet | Brad Sweet continues early season dominance by winning at Beaver Dam Raceway, extending his points lead over Donny Schatz |
| Friday, July 12, 2019 | WoO | Hartford,MI | | 23 | David Gravel | EYE ON THE PRIZE: David Gravel makes late race pass to win at Hartford Speedway |
| Saturday, August 10, 2019 | WoO | Knoxville,IA | Knoxville Nationals | 109 | David Gravel | David Gravel On Top of Sprint Car World with Triumph at 59th Annual NOS Energy Drink Knoxville Nationals Presented by Casey’s General Stores! |
| Friday, August 23, 2019 | WoO | Black Hills,SD | Rushmore Outlaw Showdown | 18 | Carson Macedo | Carson Macedo overtakes Shane Stewart on an early restart for the lead and powers to his third win of the season |
| Saturday, August 24, 2019 | WoO | Big Sky,MT | | 21 | David Gravel | David Gravel picks up his seventh win of the season, first Big Sky Speedway win |
| Friday, August 30, 2019 | WoO | Skagit,WA | | 19 | Logan Schuchart | Logan Schuchart dominated the 30-lap event to win his fifth race of the season |
| Saturday, August 31, 2019 | WoO | Skagit,WA | | 21 | Logan Schuchart | Logan Schuchart sweeps Skagit Speedway doubleheader |
| Monday, September 2, 2019 | WoO | Grays Harbor,WA | | 17 | Daryn Pittman | LABORING VICTORY: Daryn Pittman wins Labor Day race at Grays Harbor Raceway |
| Wednesday, September 25, 2019 | WoO | Jacksonville,IL | | 36 | Carson Macedo | Carson Macedo wins thrilling show at Jacksonville Speedway |
| Saturday, October 5, 2019 | WoO | Williams Grove,PA | National Open | 49 | Brent Marks | Brent Marks wins the National Open at Williams Grove Speedway |
| Saturday, November 9, 2019 | WoO | Charlotte,NC | World Finals | 53 | David Gravel | Sweet beats Donny Schatz by 4 points in closest points battle in Series history; David Gravel sweeps Can-Am World Finals |
