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| 5/5/2023 | Princeton Speedway - Princeton, MN Season Opener, 3rd try + Micros Winged A-Class, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Jacob Earl (Winged A-Class) | 2nd | - | - | 14th (DNF) |
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| 5/26/2023 | Princeton Speedway - Princeton, MN Regular Racing + Micros (No Supers) Winged A-Class, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact, WISSOTA Mod Four | Results | | Jacob Earl (Winged A-Class) | 5th | - | - | DNS |
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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 | | Jacob Earl (Winged A-Class) | 4th | - | - | 8th |
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| 6/3/2023 | Ogilvie Raceway - Ogilvie, MN World of Outlaws Sprint Car Night 410 Sprints - Winged: World of Outlaws Winged A-Class, WISSOTA Midwest Mods | Results | | Jacob Earl (Winged A-Class) | 7th (DNF) | - | - | 9th |
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| 6/16/2023 | Beaver Dam Raceway - Beaver Dam, WI Jim JB Boyd Memorial with World of Outlaws Sprints Night 1 410 Sprints - Winged: World of Outlaws Winged Outlaw: Minnesota Micro Sprints Pro Legends: Midwest Legends Dirt Series | Results | | Jacob Earl (Winged Outlaw) | 1st | - | - | 2nd |
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| 6/17/2023 | Beaver Dam Raceway - Beaver Dam, WI Jim JB Boyd Memorial with World of Outlaws Sprints Night 2 410 Sprints - Winged: World of Outlaws Winged Outlaw: Minnesota Micro Sprints Pro Legends: Midwest Legends Dirt Series | Results | | Jacob Earl (Winged Outlaw) | 6th | - | - | 7th |
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| 7/14/2023 | Princeton Speedway - Princeton, MN 305 Sprints, Micro Sprints, Mini Mods, Midgets & More! Stock Cars, Winged A-Class, IMCA Northern SportMod, IMCA RaceSaver Sprint Car, IMCA Sport Compact | Results | | Jacob Earl (Winged A-Class) | 6th | - | - | 7th |
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| 8/4/2023 | Mississippi Thunder Speedway - Fountain City, WI LT Construction Night 125cc Winged Micros, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks, USRA Stock Cars | Results | | Jacob Earl (125cc Winged Micros) | 3rd | - | - | 6th |
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| 8/5/2023 | Mississippi Thunder Kart Track - Fountain City, WI Battle of the Wings Winged Sprints, Restricted 'A' Class, Non-Winged Sprints, 125cc Winged Micros, Junior Champ, Junior 1 Lites Dirt Karts, Junior 2 Lites Dirt Karts, Adult Heavy, Dirt Cage Kart Junior 1, Flat Adult Clone Heavy, 250 Winged Outlaw, LO 206 Dirt Karts, Open Dirt Karts, Junior Slingshots | Results | | Jacob Earl (Winged Sprints) | 2nd | 6th | - | 12th |
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| 8/11/2023 | Princeton Speedway - Princeton, MN Mille Lacs County Fair Races!! Winged A-Class, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Jacob Earl (Winged A-Class) | 7th (DNF) | - | - | 10th |
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| 8/12/2023 | North Central Speedway - Brainerd, MN Bud Jones & Sons Night + Micro Sprints Winged A-Class, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Jacob Earl (Winged A-Class) | 3rd | - | - | 3rd |
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| 9/1/2023 | Princeton Speedway - Princeton, MN Championship Night Winged A-Class, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Jacob Earl (Winged A-Class) | 5th | - | - | 5th |
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| 9/2/2023 | North Central Speedway - Brainerd, MN 22nd Annual Mighty Axe Nationals Winged A-Class, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Jacob Earl (Winged A-Class) | 4th | - | - | 5th |
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| 9/3/2023 | North Central Speedway - Brainerd, MN 22nd Annual Mighty Axe Nationals Winged A-Class, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Jacob Earl (Winged A-Class) | 5th | - | - | 6th |
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| 9/9/2023 | Cedar Lake Speedway - New Richmond, WI 23rd Annual Jerry Richert Memorial 360 Sprints - Winged: Midwest Power Series 410 Sprints - Winged: IRA Interstate Racing Association Winged A-Class, 305 Sprints - Non-Winged | Results | | Jacob Earl (Winged A-Class) | 7th | - | - | 6th |
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| 10/21/2023 | Ogilvie Raceway - Ogilvie, MN 13th Annual Topless Nationals - Night 2 A Modifieds, Winged A-Class, B Modifieds, Street Stocks, Dirt Late Models, Dirt 4 cyl Modifieds, Sport Compact, Super Stocks | Results | | Jacob Earl (Winged A-Class) | 6th | - | - | 7th |
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