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| 4/27/2019 | Sheridan Speedway - Sheridan, WY National Points ONLY Dirt Mini Trucks, A Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 1st | - | - | 4th |
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| 5/3/2019 | Sheridan Speedway - Sheridan, WY Sponsored by Big Horn Mountain Radio Quarter Midgets, Dirt Mini Trucks, A Modifieds, Junior Honda, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 1st | - | - | 3rd |
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| 5/10/2019 | Sheridan Speedway - Sheridan, WY Sponsored by Buckshot Saloon Quarter Midgets, Dirt Mini Trucks, A Modifieds, Dwarf, Junior Honda, WISSOTA Midwest Mods, WISSOTA Street Stock | Rain Out |
| 5/17/2019 | Casper Speedway - Casper, WY Hobby Stocks, Stock Cars, A Modifieds, Dwarf, WISSOTA Midwest Mods | Results | | Jay Will (WISSOTA Midwest Mods) | 1st | - | - | 7th |
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| 5/31/2019 | Sheridan Speedway - Sheridan, WY Farmer's Co-op and Excalibur Construction present Race of Champions - RAIN OUT DATE - July 26 Dirt Mini Trucks, A Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 2nd | - | - | 5th |
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| 6/9/2019 | Sheridan Speedway - Sheridan, WY Komatsu Equipment Company presents IMCA Gunslinger Tour - Night 1 A Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 2nd | - | - | 7th |
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| 6/10/2019 | Sheridan Speedway - Sheridan, WY Solid Construction presents IMCA Gunslinger Tour - Night 2 A Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 1st | - | - | 6th |
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| 6/14/2019 | Sheridan Speedway - Sheridan, WY Jensen/Will Mod 4 Special Quarter Midgets, Dirt Mini Trucks, Dwarf, Junior Honda, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 4th | - | - | 3rd |
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| 6/21/2019 | Sheridan Speedway - Sheridan, WY Sponsored by Morton Buildings Quarter Midgets, Dirt Mini Trucks, A Modifieds, Junior Honda, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 2nd | - | - | 2nd |
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| 6/28/2019 | Big Sky Speedway - Billings, MT June 28th Races - Wild West A Modifieds, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 1st | - | - | 7th |
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| 6/29/2019 | Big Sky Speedway - Billings, MT June 29th Races - Wild West A Modifieds, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 5th | - | DNS | - |
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| 6/30/2019 | Sheridan Speedway - Sheridan, WY Bolt Construction and Peak Power Sports present WISSOTA Wild West Tour - Night 1 A Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 3rd | - | - | 11th |
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| 7/1/2019 | Sheridan Speedway - Sheridan, WY Heartland Kubota, LLC & Bolt Construction present WISSOTA Wild West Tour - Night 2 A Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 1st | - | - | 3rd |
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| 7/19/2019 | Sheridan Speedway - Sheridan, WY Sponsored by Sheridan Community Federal Credit Union Quarter Midgets, Dirt Mini Trucks, Junior Honda, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 1st | - | - | 1st |
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| 7/26/2019 | Sheridan Speedway - Sheridan, WY Sponsored by EMIT Technologies, Inc. Dirt Mini Trucks, A Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 1st | - | - | 6th |
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| 8/9/2019 | Sheridan Speedway - Sheridan, WY Sponsored by Aaron's Dirt Mini Trucks, A Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 1st | - | - | 5th |
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| 8/16/2019 | Sheridan Speedway - Sheridan, WY Sponsored by Sheridan Motor and Deines Chiropractic Clinic Quarter Midgets, Dirt Mini Trucks, A Modifieds, Dwarf, Junior Honda, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 5th | - | - | 5th |
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| 8/30/2019 | Gillette Thunder Speedway - Gillette, WY 18th Annual East-West Clash Hobby Stocks, A Modifieds, Sport Compact, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 7th | - | - | 12th |
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| 8/31/2019 | Gillette Thunder Speedway - Gillette, WY 18th Annual East-West Clash Hobby Stocks, A Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 4th | - | - | 11th |
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| 9/6/2019 | Sheridan Speedway - Sheridan, WY Rocky Mountain Ambulance sponsors of First Responder Recognition Night Quarter Midgets, A Modifieds, Junior Honda, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 1st | - | - | 3rd |
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| 9/13/2019 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 - Day 3 WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 8th | - | - | - |
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| 9/14/2019 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 FINALE! WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 11th | - | - | - |
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| 9/27/2019 | Sheridan Speedway - Sheridan, WY I-90 Challenge - Night 1 Quarter Midgets, Dirt Mini Trucks, A Modifieds, Dwarf, Junior Honda, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Jay Will (WISSOTA Midwest Mods) | 1st | - | - | 8th |
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