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| 5/20/2023 | Cedar Lake Speedway - New Richmond, WI CLS Dash Race #4 Limited Sprints - Winged, A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 5th | - | - | 8th |
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| 5/27/2023 | Cedar Lake Speedway - New Richmond, WI Pack The Track Night / Cook Memorial Winged A-Class, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 5th | - | - | 13th |
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| 6/2/2023 | I-94 Speedway - Fergus Falls, MN Prelude to the Dick Johanneck King of Dirt w/ Dirt Race Central Street Stock Tour & Super Stocks WISSOTA Street Stock: Street Stock Tour A Modifieds, Hornets, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Super Stock | Results | | Steven O'Brien Jr (Economy Late Models) | 3rd | - | - | 15th (DNF) |
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| 6/3/2023 | I-94 Speedway - Fergus Falls, MN Dick Johanneck King of Dirt w/ NLRA LM, Dirt Race Central Street Stock Tour, and KIDS NIGHT WISSOTA Street Stock: Street Stock Tour A Modifieds, Hornets, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Steven O'Brien Jr (Economy Late Models) | 3rd | - | - | 13th (DNF) |
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| 6/9/2023 | Eagle Valley Speedway - Jim Falls, WI 9th Annual Southworth Chevy & Tim's Automotive MWM Special A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Modifieds, USRA Late Models, WISSOTA Pure Stock | Results | | Steven O'Brien Jr (USRA Late Models) | 3rd | - | - | 4th |
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| 6/15/2023 | Cedar Lake Speedway - New Richmond, WI 24th Annual Masters (Day 1 of 3) A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 5th | - | - | 9th |
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| 6/16/2023 | Cedar Lake Speedway - New Richmond, WI 24th Annual Masters (Day 2 of 3) A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 1st | - | - | 6th |
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| 6/17/2023 | Cedar Lake Speedway - New Richmond, WI 24th Annual Masters (Day 3 of 3) A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 7th | - | - | 12th (DNF) |
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| 7/1/2023 | Rice Lake Speedway - Rice Lake, WI USRA Late Models Plus Pures, Streets, MWM, Supers Open Dirt Karts, USRA Late Models, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, Flat Jr. 2 Clone Heavy | Results | | Steven O'Brien Jr (USRA Late Models) | 5th | - | - | 6th |
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| 7/3/2023 | Tomahawk Speedway - Tomahawk, WI July 4th Special Stock Cars, Winged A-Class, B Modifieds, Street Stocks, Kid Karts Dirt, Pure Stock, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | 3rd | - | - | 5th |
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| 7/7/2023 | Eagle Valley Speedway - Jim Falls, WI Vintage Modifieds: Northern Vintage Stockcar Racers A Modifieds, B Modifieds, Street Stocks, Vintage Full Body Stock Cars, Hornets, Super Stocks, USRA Late Models, WISSOTA Pure Stock | Results | | Steven O'Brien Jr (USRA Late Models) | 1st | - | - | 9th |
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| 8/18/2023 | Eagle Valley Speedway - Jim Falls, WI 22nd Annual Krug Towing & Chuck's Ripp's Bar & Grill Lonnie Leu Memorial A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Modifieds, USRA Late Models, WISSOTA Pure Stock | Results | | Steven O'Brien Jr (USRA Late Models) | 3rd | - | - | 4th |
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| 8/19/2023 | Cedar Lake Speedway - New Richmond, WI CLS Dash Race #12 Limited Sprints - Winged, A Modifieds, Midwest Modifieds, USRA Late Models, WISSOTA Super Stock | Results | | Steven O'Brien Jr (USRA Late Models) | 4th | - | - | 7th |
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| 8/25/2023 | Eagle Valley Speedway - Jim Falls, WI Baxter Engines/Baxter's Speed Shop - Season Championships A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Late Models, WISSOTA Pure Stock | Results | | Steven O'Brien Jr (USRA Late Models) | 4th | - | - | 4th |
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| 8/26/2023 | Cedar Lake Speedway - New Richmond, WI CLS Dash Race #13 / Season Championship A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, USRA Late Models, WISSOTA Super Stock | Results | | Steven O'Brien Jr (USRA Late Models) | 6th | - | - | 10th |
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| 9/8/2023 | Eagle Valley Speedway - Jim Falls, WI Jim Town Showdown - Parsons Trophy Tour A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Modifieds, USRA Late Models, WISSOTA Pure Stock | Results | | Steven O'Brien Jr (USRA Late Models) | 1st | - | - | 15th |
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| 9/9/2023 | Gondik Law Speedway - Superior, WI Northern Nationals-Night #3 USRA Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Rain Out |
| 9/14/2023 | Cedar Lake Speedway - New Richmond, WI Legendary 100 Day 1 Limited Sprints - Winged, A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Pure Stock, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | - | - | - | 13th |
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| 9/15/2023 | Cedar Lake Speedway - New Richmond, WI Legendary 100 Day 2 Limited Sprints - Winged, A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Pure Stock, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | - | - | - | 9th |
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| 9/16/2023 | Cedar Lake Speedway - New Richmond, WI Legendary 100 Day 3 / Features Limited Sprints - Winged, A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Pure Stock, USRA Late Models | Results | | Steven O'Brien Jr (USRA Late Models) | - | - | - | 9th |
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| 9/29/2023 | Mississippi Thunder Speedway - Fountain City, WI The Great Pumpkin Race Open Dirt Karts, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, USRA Stock Cars | Results | | Steven O'Brien Jr (USRA Late Models) | 5th | - | - | 19th (DNF) |
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