| 5/3/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Late Model | | Rain Out |
| 5/10/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Late Model | | Rain Out |
| 5/17/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, WISSOTA Late Model, WISSOTA Midwest Mods, WISSOTA Street Stock | | Results |
| 5/24/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Late Model | | Rain Out |
| 5/31/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Late Model | | Results |
| 6/7/2019 | 410 Sprints - Winged: World of Outlaws WISSOTA Late Model | | Results |
| 6/14/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, WISSOTA Late Model, WISSOTA Midwest Mods, WISSOTA Street Stock | | Results |
| 6/21/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association Lightning Sprints, WISSOTA Street Stock | | Results |
| 6/23/2019 | B Modifieds, Legends, Lightning Sprints, WISSOTA Midwest Mods, WISSOTA Late Model | | Results |
| 6/28/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock | | Results |
| 7/5/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Late Model | | Results |
| 7/12/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models, B Modifieds, WISSOTA Modifieds | | Results |
| 7/19/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, WISSOTA Late Model, WISSOTA Midwest Mods, WISSOTA Street Stock | | Results |
| 7/26/2019 | B Modifieds, Lightning Sprints, WISSOTA Street Stock, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Modifieds | | Results |
| 8/2/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock | | Results |
| 8/9/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, Lightning Sprints, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Late Model | | Results |
| 8/16/2019 | 410 Sprints - Winged: World of Outlaws WISSOTA Late Model | | Results |
| 8/23/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Modifieds | | Results |
| 8/30/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series B Modifieds, Western Renegade Wingless Sprints, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Late Model | | Results |
| 9/5/2019 | B Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Late Model | | Results |
| 9/6/2019 | 410 Sprints - Winged: Northern Outlaw Sprint Association B Modifieds, WISSOTA Late Model, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Midwest Mods | | Results |
| 9/7/2019 | Dirt Late Models, B Modifieds, Street Stocks, WISSOTA Modifieds | | Results |
| 9/13/2019 | 410 Sprints - Winged, Legends, Lightning Sprints, IMCA Northern Sports Mod, IMCA Hobby Stocks | | Rain Out |