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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 | | Steven O'Brien Jr (USRA B-Mods) | 9th (DNF) | - | 14th | - |
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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 | | Steven O'Brien Jr (USRA B-Mods) | 7th (DNF) | - | DNS | - |
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| 5/30/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #5 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Modifieds | Results | | Steven O'Brien Jr (Midwest Modifieds) | 7th | - | 9th | - |
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| 6/6/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #6 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Steven O'Brien Jr (Midwest Modifieds) | 8th (DNF) | - | DNS | - |
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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 | | Steven O'Brien Jr (USRA B-Mods) | 4th | - | - | 22nd (DNF) |
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| 6/13/2020 | Deer Creek Speedway - Spring Valley, MN School Bus Races-Mascot Night-Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Steven O'Brien Jr (USRA B-Mods) | 4th | - | - | 22nd (DNF) |
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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 | | Steven O'Brien Jr (USRA B-Mods) | 4th | - | - | 16th |
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| 6/20/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #7 & Kids Night Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Super Stocks | Results | | Steven O'Brien Jr (Midwest Modifieds) | 8th (DNF) | - | DNS | - |
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| 7/2/2020 | Mississippi Thunder Speedway - Fountain City, WI Dirt Late Models, USRA B-Mods, USRA Modifieds | Results | | Steven O'Brien Jr (USRA B-Mods) | 6th | - | - | 17th |
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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 | | Steven O'Brien Jr (USRA B-Mods) | 8th | - | - | 21st (DNF) |
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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 | | Steven O'Brien Jr (USRA B-Mods) | 6th | - | - | 13th |
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| 7/17/2020 | Chateau Speedway - Lansing, MN UMSS Traditional Non Wing Sprints 360 Sprints - Non-Winged, Pure Stock, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Steven O'Brien Jr (USRA B-Mods) | 4th | - | - | 12th |
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| 7/22/2020 | Fayette County Speedway - West Union, IA 2020 Fayette County Fair Race - 1st Annual FCS Late Model Showdown - $4,000 to win/$400 to start! Dirt Late Models, USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars | Results | | Steven O'Brien Jr (USRA B-Mods) | 8th | - | - | 10th |
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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 | | Steven O'Brien Jr (USRA B-Mods) | 8th | - | 9th | - |
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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 | | Steven O'Brien Jr (Midwest Modifieds) | 9th | - | 18th | - |
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| 8/7/2020 | Chateau Speedway - Lansing, MN Traditional Non Wing Sprints - Fireworks 360 Sprints - Non-Winged, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Steven O'Brien Jr (USRA B-Mods) | 5th | - | - | 9th |
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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 | | Steven O'Brien Jr (USRA B-Mods) | 8th | - | - | 21st |
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| 8/15/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #13 A Modifieds, Midwest Modifieds, 600cc Modifieds, Super Stocks, USRA Modifieds, USRA Late Models | Results | | Steven O'Brien Jr (Midwest Modifieds) | 6th | - | 8th | - |
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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 | | Steven O'Brien Jr (USRA B-Mods) | 4th | - | - | 16th |
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| 8/22/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #14 & Season Championship 360 Sprints - Non-Winged: Traditional Sprint Car Series DIRTcar UMP Modifieds, A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Modifieds, USRA Late Models | Results | | Steven O'Brien Jr (Midwest Modifieds) | 7th | - | 2nd | 22nd |
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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 | | Steven O'Brien Jr (USRA B-Mods) | 4th | - | - | 14th |
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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 | | Steven O'Brien Jr (USRA B-Mods) | 9th | - | 10th | - |
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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 | | Steven O'Brien Jr (USRA B-Mods) | 7th | - | 7th | - |
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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 | | Steven O'Brien Jr (USRA B-Mods) | 8th | - | 11th | - |
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| 9/16/2020 | Cedar Lake Speedway - New Richmond, WI Open Practice : All Classes 6-9pm A Modifieds, Midwest Modifieds, Dirt Late Models, WISSOTA Midwest Mods | Results | | Steven O'Brien Jr (Midwest Modifieds) | - | - | - | - |
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| 9/17/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 1 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Steven O'Brien Jr (Midwest Modifieds) | - | - | - | 16th (DNF) | | Steven O'Brien Jr (USRA Late Models) | - | - | - | 12th |
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| 9/18/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 2 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Steven O'Brien Jr (Midwest Modifieds) | - | - | - | - | | Steven O'Brien Jr (USRA Late Models) | - | - | - | 13th |
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| 9/19/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 3 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Steven O'Brien Jr (Midwest Modifieds) | - | - | 12th | - | | Steven O'Brien Jr (USRA Late Models) | - | - | - | 18th (DNF) |
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| 9/25/2020 | Cedar Lake Speedway - New Richmond, WI Fall Frenzy Day 1 A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks, USRA Late Models | Results | | Steven O'Brien Jr (Midwest Modifieds) | 8th | - | 5th | - | | Steven O'Brien Jr (USRA Late Models) | 5th | - | - | 10th |
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| 9/26/2020 | Cedar Lake Speedway - New Richmond, WI Fall Frenzy Day 2 A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks, Pure Stock, USRA Late Models | Results | | Steven O'Brien Jr (Midwest Modifieds) | - | - | - | - | | Steven O'Brien Jr (USRA Late Models) | - | - | - | - |
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| 10/2/2020 | Chateau Speedway - Lansing, MN 3rd Annual Extravaganza Night 1 Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Steven O'Brien Jr (USRA B-Mods) | 7th | - | - | 17th |
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