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| 4/26/2019 | Mississippi Thunder Speedway - Fountain City, WI Season Opener A Modifieds, Hornets, 600cc Modifieds, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, All Star Slingshots | Results | | Ryan Olson (USRA B-Mods) | 1st | - | - | 6th |
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| 5/3/2019 | Mississippi Thunder Speedway - Fountain City, WI Regular Races Hornets, 600cc Modifieds, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, All Star Slingshots | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 2nd |
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| 5/10/2019 | Mississippi Thunder Speedway - Fountain City, WI The Rumble by the River 40 Presented by Napa Dirt Late Models: Dirt Kings Late Model Tour USRA B-Mods, USRA Modifieds, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 5th |
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| 5/24/2019 | Mississippi Thunder Speedway - Fountain City, WI 11th Annual USMTS Event A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 2nd |
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| 5/31/2019 | Mississippi Thunder Speedway - Fountain City, WI Fastenal Night 600cc Modifieds, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, All Star Slingshots, WISSOTA Modifieds | Results | | Ryan Olson (USRA B-Mods) | 1st | - | - | 2nd |
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| 6/7/2019 | Mississippi Thunder Speedway - Fountain City, WI Leighton Broadcasting & Bud Night Hornets, 600cc Modifieds, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, All Star Slingshots | Results | | Ryan Olson (USRA B-Mods) | 3rd | - | - | 4th | | Ryan Olson (USRA Modifieds) | DNS | - | - | 11th |
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| 7/4/2019 | Mississippi Thunder Speedway - Fountain City, WI Rivercity Rumble Night #1 WISSOTA Late Model: Wissota Late Model Challenge Series USRA B-Mods, USRA Modifieds, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 1st | - | - | 1st |
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| 7/5/2019 | Mississippi Thunder Speedway - Fountain City, WI Rivercity Rumble Night #2 WISSOTA Late Model: Wissota Late Model Challenge Series USRA B-Mods, USRA Modifieds, USRA Hobby Stocks, WISSOTA Modifieds | Results | | Ryan Olson (USRA B-Mods) | 4th | - | - | 5th |
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| 7/12/2019 | Mississippi Thunder Speedway - Fountain City, WI Regular Races Hornets, 600cc Modifieds, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, All Star Slingshots | Results | | Ryan Olson (USRA B-Mods) | 3rd | - | - | 1st |
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| 7/26/2019 | Mississippi Thunder Speedway - Fountain City, WI Baehman Law Challenge Night Hornets, 600cc Modifieds, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, All Star Slingshots | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 6th |
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| 8/2/2019 | Mississippi Thunder Speedway - Fountain City, WI Regular Races Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 2nd |
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| 8/16/2019 | Mississippi Thunder Speedway - Fountain City, WI Johnny Severtson Memorial Swarm Hornets, USRA B-Mods, USRA Modifieds, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 5th |
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| 8/23/2019 | Mississippi Thunder Speedway - Fountain City, WI Season Championship Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 1st |
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| 8/30/2019 | Mississippi Thunder Speedway - Fountain City, WI 7th Annual USMTS Event A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 2nd |
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| 9/6/2019 | Mississippi Thunder Speedway - Fountain City, WI Mod Nationals Night #1 USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, WISSOTA Modifieds | Results | | Ryan Olson (USRA B-Mods) | 1st | - | - | - |
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| 9/7/2019 | Mississippi Thunder Speedway - Fountain City, WI Mod National Night #2 USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, WISSOTA Modifieds | Results | | Ryan Olson (USRA B-Mods) | - | - | - | 10th |
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| 9/13/2019 | Cedar Lake Speedway - New Richmond, WI Legendary 100 night 2 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks | Results | | Ryan Olson (Midwest Modifieds) | 5th | - | - | - |
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| 9/14/2019 | Cedar Lake Speedway - New Richmond, WI Legendary 100 night 3 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks | Results | | Ryan Olson (Midwest Modifieds) | - | - | - | 6th |
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