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| 4/3/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #1 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 1st | - | - | 5th |
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| 4/16/2021 | Cedar Lake Speedway - New Richmond, WI Legendary Opener Day 2 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | - | - | - | 10th |
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| 4/17/2021 | Cedar Lake Speedway - New Richmond, WI Legendary Open Day 3 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | - | - | - | 11th |
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| 4/23/2021 | Mississippi Thunder Speedway - Fountain City, WI 13th Annual Season Opener presented by Kelly Iverson Trucking Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Steven O'Brien Jr (USRA Late Models) | 4th | - | - | 9th |
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| 4/30/2021 | 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 Late Models) | 5th | - | - | 8th |
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| 5/1/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #4 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 2nd | - | - | 7th |
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| 5/7/2021 | Eagle Valley Speedway - Jim Falls, WI UMSS Sprint Car Showdown Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 360 Sprints - Winged, A Modifieds, B Modifieds, Street Stocks, Winged Outlaw, Hornets, Super Stocks, Pure Stock, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 4th | - | - | 2nd |
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| 5/14/2021 | Mississippi Thunder Speedway - Fountain City, WI Weekly Racing Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Rain Out |
| 5/15/2021 | Deer Creek Speedway - Spring Valley, MN Points Race A Modifieds, USRA B-Mods, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Steven O'Brien Jr (USRA Late Models) | 4th | - | - | 7th |
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| 5/22/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #5 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 6th | - | - | 4th |
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| 6/4/2021 | Mississippi Thunder Speedway - Fountain City, WI 13th Annual Rivercity Rumble Dirt Super Late Models: Lucas Oil MLRA USRA B-Mods, USRA Modifieds, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 3rd | - | - | 14th |
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| 6/11/2021 | 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 Late Models) | 5th | - | - | 8th |
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| 6/12/2021 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Steven O'Brien Jr (USRA Late Models) | 5th | - | - | 8th |
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| 6/17/2021 | Cedar Lake Speedway - New Richmond, WI 22nd Annual Masters A Modifieds, Dirt Late Models, USRA Modifieds, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 8th | - | - | 22nd |
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| 6/18/2021 | Cedar Lake Speedway - New Richmond, WI 22nd Annual Masters A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Late Models, WISSOTA Modifieds | Results | | Steven O'Brien Jr (USRA Late Models) | 9th | - | 4th | 23rd (DNF) |
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| 6/19/2021 | Cedar Lake Speedway - New Richmond, WI 22nd Annual Masters Limited Sprints - Winged: Upper Midwest Sprint Car Series A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Late Models, WISSOTA Modifieds | Results | | Steven O'Brien Jr (USRA Late Models) | 8th | - | - | 14th |
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| 7/2/2021 | Mississippi Thunder Speedway - Fountain City, WI Karl Fenske Memorial Dirt Late Models, Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Steven O'Brien Jr (USRA Late Models) | 3rd | - | - | 13th |
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| 7/9/2021 | Eagle Valley Speedway - Jim Falls, WI Don Hazelton Memorial - Kids's Night A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, Pure Stock, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 4th | - | - | 8th |
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| 7/10/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #9 / Modified $5,000 To Win A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 6th | - | - | 7th |
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| 7/16/2021 | Mississippi Thunder Speedway - Fountain City, WI USRA Late Model Special 125cc Winged Micros, Hornets, USRA B-Mods, USRA Late Models, USRA Hobby Stocks | Results | | Steven O'Brien Jr (USRA Late Models) | 5th | - | - | 5th |
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| 7/17/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #10 / Pro Stock $5,000 To Win 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 305 Sprints - Non-Winged, 600cc Modifieds, Super Stocks, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 5th | - | - | 15th (DNF) |
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| 7/23/2021 | Mississippi Thunder Speedway - Fountain City, WI Weekly Racing USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Steven O'Brien Jr (USRA Late Models) | 3rd | - | - | 6th |
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| 7/24/2021 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Steven O'Brien Jr (USRA Late Models) | 5th | - | - | 2nd |
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| 7/30/2021 | Mississippi Thunder Speedway - Fountain City, WI K-Town Klash USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | Steven O'Brien Jr (USRA Late Models) | 5th | - | - | 9th |
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| 7/31/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #12 / Midwest Mod $5,000 To Win A Modifieds, Midwest Modifieds, Super Stocks, USRA Late Models, WISSOTA Street Stock | Results | | Steven O'Brien Jr (USRA Late Models) | 6th | - | - | 16th (DNF) |
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| 8/5/2021 | Cedar Lake Speedway - New Richmond, WI 34th Annual USA Nationals Night 1 Dirt Super Late Models: World of Outlaws - Late Models USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 8th | - | - | 11th (DNF) |
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| 8/6/2021 | 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 Late Models) | 7th | - | - | 15th (DNF) |
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| 8/14/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #13 / Heros Night A Modifieds, Midwest Modifieds, Super Stocks, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | DNS | - | - | 14th |
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| 8/20/2021 | Eagle Valley Speedway - Jim Falls, WI 20th Annual Lonnie Leu Memorial presented by Krug's Towing & EVS A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, Pure Stock, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 3rd | - | - | 5th |
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| 8/21/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #14 / Season Championship 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 6th | - | - | 10th |
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| 9/4/2021 | Deer Creek Speedway - Spring Valley, MN 16th Annual USMTS Labor Day Duel A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods, USRA Late Models, USRA Stock Cars | Results | | Steven O'Brien Jr (USRA Late Models) | 6th | - | - | 8th |
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| 9/10/2021 | Eagle Valley Speedway - Jim Falls, WI 2nd Annual - Dalbeck Logging - Union Trailer & Power Equipment Jim Town Showdown A Modifieds, B Modifieds, Street Stocks, Super Stocks, Pure Stock, USRA Late Models, WISSOTA Modifieds | Results | | Steven O'Brien Jr (USRA Late Models) | 4th | - | - | 15th |
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| 9/16/2021 | Cedar Lake Speedway - New Richmond, WI 16th Annual Legendary 100 Night 1 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models, WISSOTA Midwest Mods | Results | | Steven O'Brien Jr (USRA Late Models) | - | - | - | 17th |
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| 9/17/2021 | Cedar Lake Speedway - New Richmond, WI 16th Annual Legendary 100 Night 2 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models, WISSOTA Midwest Mods | Results | | Steven O'Brien Jr (USRA Late Models) | - | - | - | 8th |
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| 9/18/2021 | Cedar Lake Speedway - New Richmond, WI 16th Annual Legendary 100 Night 3 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models, WISSOTA Midwest Mods | Results | | Steven O'Brien Jr (USRA Late Models) | - | - | - | 16th |
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| 10/1/2021 | Mississippi Thunder Speedway - Fountain City, WI The Great Pumpkin Race Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, USRA Stock Cars | Results | | Steven O'Brien Jr (USRA Late Models) | 3rd | - | - | 20th (DNF) |
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| 10/2/2021 | Mississippi Thunder Speedway - Fountain City, WI The Great Pumpkin Race Hornets, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, USRA Stock Cars | Results | | Steven O'Brien Jr (USRA Late Models) | 7th | - | - | DNS |
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