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| 5/1/2020 | Mississippi Thunder Speedway - Fountain City, WI Weekly Racing Dirt Late Models, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 1st | - | - | 1st |
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| 5/15/2020 | Mississippi Thunder Speedway - Fountain City, WI Weekly Racing Dirt Late Models, Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 3rd | - | - | 4th |
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| 5/22/2020 | Mississippi Thunder Speedway - Fountain City, WI USMTS Spring Shootout and Rumble by the River 40 Presented by Coca-Cola A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA B-Mods, USRA Modifieds, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 1st | - | - | 3rd |
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| 5/23/2020 | Cedar Lake Speedway - New Richmond, WI Pack The Track Night and Cook Memorial FREE GRANDSTAND ENTRY! Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Midwest Modifieds, Winged A-Class, Pony Stock, Super Stocks, USRA Late Models | Results | | Ryan Olson (Midwest Modifieds) | 3rd | - | - | 10th |
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| 5/29/2020 | Mississippi Thunder Speedway - Fountain City, WI Military Night Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, WISSOTA Super Stock | Results | | Ryan Olson (USRA B-Mods) | 6th (DNF) | - | DNS | - |
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| 6/5/2020 | Mississippi Thunder Speedway - Fountain City, WI Leighton Broadcasting/Bud Night Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 2nd |
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| 6/12/2020 | Mississippi Thunder Speedway - Fountain City, WI Beahman Law Redneck 100 Challenge Hornets, USRA B-Mods, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 1st | - | - | 5th |
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| 6/19/2020 | Mississippi Thunder Speedway - Fountain City, WI Weekly Racing Action Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 4th |
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| 6/26/2020 | Mississippi Thunder Speedway - Fountain City, WI Weekly Racing Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 3rd | - | - | 1st |
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| 7/2/2020 | Mississippi Thunder Speedway - Fountain City, WI Dirt Late Models, USRA B-Mods, USRA Modifieds | Results | | Ryan Olson (USRA B-Mods) | 1st | - | - | 1st |
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| 7/3/2020 | Mississippi Thunder Speedway - Fountain City, WI Rivercity Rumble - Firecracker 40 presented by Rivercity MFG Dirt Late Models, USRA B-Mods, USRA Modifieds, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 1st | - | - | 1st |
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| 7/10/2020 | Mississippi Thunder Speedway - Fountain City, WI Weekly Racing Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 3rd | - | - | 1st |
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| 7/17/2020 | Mississippi Thunder Speedway - Fountain City, WI Karl Fenske Memorial USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 3rd | | Ryan Olson (USRA Modifieds) | 7th (DNF) | - | 4th | 20th (DNF) |
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| 7/24/2020 | Mississippi Thunder Speedway - Fountain City, WI Severson Oil Night Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 3rd |
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| 7/31/2020 | Mississippi Thunder Speedway - Fountain City, WI K-Town Klash Casey Knutson Memorial USRA B-Mods, USRA Modifieds, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 5th | - | 2nd | 21st |
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| 8/1/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #12 A Modifieds, Midwest Modifieds, Super Stocks, USRA Late Models | Results | | Ryan Olson (Midwest Modifieds) | 3rd | - | 3rd | 24th | | Ryan Olson (USRA Late Models) | 2nd | - | - | 13th |
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| 8/6/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models USRA Late Models | Results | | Ryan Olson (USRA Late Models) | 2nd | - | - | 10th |
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| 8/14/2020 | Mississippi Thunder Speedway - Fountain City, WI USRA Late Model Special presented by RJ'S Fast Tracks & Two Brother's Auto Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 3rd | - | - | 7th | | Ryan Olson (USRA Late Models) | 1st | - | - | 4th |
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| 8/21/2020 | Mississippi Thunder Speedway - Fountain City, WI Dairyland Showdown Presented by Hurco/Stone Machinery Dirt Late Models, USRA B-Mods, USRA Modifieds, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | - | 4th |
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| 8/28/2020 | Mississippi Thunder Speedway - Fountain City, WI 12th Annual Season Championship Night Dirt Late Models, Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Ryan Olson (USRA B-Mods) | 3rd | - | - | 1st | | Ryan Olson (USRA Late Models) | 4th | - | - | 2nd |
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| 9/10/2020 | Mississippi Thunder Speedway - Fountain City, WI 9th Annual Modified Nationals Presented by Dahl Chevy/GMC USRA B-Mods, USRA Modifieds, IMCA Modified | Results | | Ryan Olson (USRA B-Mods) | 2nd | - | 1st | 12th |
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| 9/11/2020 | Mississippi Thunder Speedway - Fountain City, WI 9th Annual Modified Nationals Presented by Dahl Chevy/GMC USRA B-Mods, USRA Modifieds, IMCA Modified | Results | | Ryan Olson (USRA B-Mods) | 4th | - | 17th (DNF) | - |
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| 9/12/2020 | Mississippi Thunder Speedway - Fountain City, WI 9th Annual Modified Nationals Presented by Dahl Chevy/GMC USRA B-Mods, USRA Modifieds, IMCA Modified | Results | | Ryan Olson (USRA B-Mods) | 3rd | - | - | 9th |
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| 9/25/2020 | Deer Creek Speedway - Spring Valley, MN A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods, IMCA Modified | Results | | Ryan Olson (USRA B-Mods) | 3rd | - | - | 29th |
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| 9/26/2020 | Deer Creek Speedway - Spring Valley, MN A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods, IMCA Modified | Results | | Ryan Olson (USRA B-Mods) | 6th | - | 2nd | 19th |
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