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| 5/8/2020 | US 36 Raceway - Osborn, MO Weekly Racing Series 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Limited Sport Mod, Pure Stock | Results | | Connor Masoner (Stock Cars) | 3rd | - | - | 8th |
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| 5/9/2020 | Bethany Fairgrounds Speedway - Bethany, MO Season Championship Race 305 Sprints - Winged, A Modifieds, B Modifieds, Street Stocks, Limited Sport Mod, Pure Stock, IMCA RaceSaver Sprint Car | Results | | Connor Masoner (Street Stocks) | 5th | - | - | 6th | | Connor Masoner (Pure Stock) | - | - | - | - |
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| 5/30/2020 | I-35 Speedway - Winston, MO Casey's Night at the Races Hobby Stocks, Midwest Modifieds, Dirt Late Models, Vintage Full Body Stock Cars, Lightning Sprints, Sport Compact, USRA B-Mods, USRA Modifieds, USRA Stock Cars | Results | | Connor Masoner (USRA Stock Cars) | 6th | - | - | 8th |
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| 6/6/2020 | Bethany Fairgrounds Speedway - Bethany, MO POWRi Iowa Sprint Car League at Bethany Fairgrounds Speedway Non-Winged Sprints: POWRi WAR Sprints with Iowa Sprint Car League A Modifieds, B Modifieds, Street Stocks, 360 Sprints - Non-Winged, Limited Sport Mod, Pure Stock, IMCA RaceSaver Sprint Car | Results | | Connor Masoner (Street Stocks) | 3rd | - | - | 3rd | | Connor Masoner (Pure Stock) | 9th | - | - | DNS |
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| 6/12/2020 | US 36 Raceway - Osborn, MO Weekly Racing Series + Non-Winged Sprints 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Non-Winged Sprints, Limited Sport Mod, Pure Stock | Results | | Connor Masoner (Stock Cars) | 8th | - | - | 11th |
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| 6/26/2020 | US 36 Raceway - Osborn, MO Doyle Lance Remembrance Race + Weekly Racing Series 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Limited Sport Mod, Pure Stock | Results | | Connor Masoner (Stock Cars) | 1st | - | - | 14th (DNF) |
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| 6/27/2020 | Bethany Fairgrounds Speedway - Bethany, MO USAC Midwest Wingless Racing Association + Season Championship Race A Modifieds, Midwest Modifieds, B Modifieds, Street Stocks, Non-Winged Sprints, Limited Sport Mod, Pure Stock, IMCA RaceSaver Sprint Car | Results | | Connor Masoner (Street Stocks) | 2nd | - | - | 8th |
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| 7/4/2020 | US 36 Raceway - Osborn, MO July 4 Special Stock Cars, A Modifieds, B Modifieds, Pure Stock | Results | | Connor Masoner (Stock Cars) | 3rd | - | - | 3rd |
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| 7/10/2020 | US 36 Raceway - Osborn, MO Weekly Racing Series 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Limited Sport Mod, Pure Stock | Results | | Connor Masoner (Stock Cars) | 1st | - | - | 19th (DNF) |
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| 7/18/2020 | Bethany Fairgrounds Speedway - Bethany, MO Season Championship Race A Modifieds, B Modifieds, Street Stocks, Limited Sport Mod, Pure Stock, IMCA RaceSaver Sprint Car | Results | | Connor Masoner (Street Stocks) | 5th | - | - | 11th (DNF) |
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| 7/24/2020 | US 36 Raceway - Osborn, MO 4th Annual Joe Crist Memorial Stock Car Shootout 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Limited Sport Mod, Pure Stock | Results | | Connor Masoner (Stock Cars) | 4th | - | - | 15th | | Connor Masoner (Pure Stock) | 1st | - | - | 1st |
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| 7/25/2020 | Bethany Fairgrounds Speedway - Bethany, MO Season Championship Race A Modifieds, B Modifieds, Street Stocks, Limited Sport Mod, Pure Stock, IMCA RaceSaver Sprint Car | Results | | Connor Masoner (Street Stocks) | 5th | - | - | 9th |
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| 8/1/2020 | Bethany Fairgrounds Speedway - Bethany, MO Valor Racing Night - Season Championship Race A Modifieds, B Modifieds, Street Stocks, 360 Sprints - Non-Winged, Limited Sport Mod, Pure Stock, IMCA RaceSaver Sprint Car | Results | | Connor Masoner (Street Stocks) | 2nd | - | - | 5th |
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| 8/7/2020 | US 36 Raceway - Osborn, MO Weekly Racing Series 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Limited Sport Mod, Pure Stock | Rain Out |
| 8/21/2020 | US 36 Raceway - Osborn, MO POWRi Iowa Sprint Car League at US 36 Raceway Non-Winged Sprints: Midwest Wingless Racing Association 305 Sprints - Winged, Stock Cars, A Modifieds, Pure Stock | Results | | Connor Masoner (Stock Cars) | 1st | - | - | 9th |
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| 8/22/2020 | Bethany Fairgrounds Speedway - Bethany, MO Non-Winged Sprints: Iowa Sprint Car League A Modifieds, B Modifieds, Street Stocks, Limited Sport Mod, Pure Stock, IMCA RaceSaver Sprint Car | Results | | Connor Masoner (Street Stocks) | 3rd | - | - | 9th (DNF) |
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| 9/4/2020 | US 36 Raceway - Osborn, MO Weekly Racing Series + E-Mod and Pure Stock Nationals Stock Cars, A Modifieds, B Modifieds, Limited Sport Mod, Pure Stock | Results | | Connor Masoner (Stock Cars) | 6th | - | - | 13th (DNF) | | Connor Masoner (Pure Stock) | 1st | - | - | 1st |
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| 9/5/2020 | Bethany Fairgrounds Speedway - Bethany, MO Season Championship Race A Modifieds, B Modifieds, Street Stocks, Limited Sport Mod, Pure Stock | Results | | Connor Masoner (Street Stocks) | 3rd | - | - | DNS | | Connor Masoner (Pure Stock) | 2nd | - | - | 6th |
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| 9/6/2020 | Bethany Fairgrounds Speedway - Bethany, MO Northwest Missouri State Fair Non-Winged Sprints: Iowa Sprint Car League A Modifieds, B Modifieds, Street Stocks, Limited Modified, Limited Sport Mod, Pure Stock | Results | | Connor Masoner (Pure Stock) | - | - | - | 1st |
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| 9/9/2020 | Boone Speedway - Boone, IA 2020 IMCA Speedway Motors Super Nationals Fueled by Casey’s IMCA Modified, IMCA Stock Car | Results | | Connor Masoner (IMCA Stock Car) | 6th | - | - | - |
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| 9/10/2020 | Boone Speedway - Boone, IA 2020 IMCA Speedway Motors Super Nationals Fueled by Casey’s Midwest Modifieds, Vintage Full Body Stock Cars, IMCA Modified, IMCA Stock Car | Results | | Connor Masoner (IMCA Stock Car) | 5th | - | 9th | - |
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| 9/11/2020 | Boone Speedway - Boone, IA 2020 IMCA Speedway Motors Super Nationals Fueled by Casey’s Generic 2, IMCA Modified, IMCA Stock Car | Results | | Connor Masoner (IMCA Stock Car) | 4th | - | DNS | - |
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| 9/25/2020 | US 36 Raceway - Osborn, MO Championship Night 305 Sprints - Winged, Stock Cars, A Modifieds, B Modifieds, Limited Sport Mod, Pure Stock | Results | | Connor Masoner (Stock Cars) | - | - | - | 9th (DNF) |
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| 9/26/2020 | Bethany Fairgrounds Speedway - Bethany, MO Championship Night A Modifieds, B Modifieds, Street Stocks, Limited Sport Mod, Pure Stock, IMCA RaceSaver Sprint Car | Results | | Connor Masoner (Street Stocks) | - | - | - | 4th |
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| 10/9/2020 | US 36 Raceway - Osborn, MO 2nd Annual IMCA Missouri Nationals Night #1 305 Sprints - Winged, Stock Cars, A Modifieds, Limited Sport Mod | Results | | Connor Masoner (Stock Cars) | 2nd | - | - | 4th |
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| 10/10/2020 | US 36 Raceway - Osborn, MO 2nd Annual IMCA Missouri Nationals Night #2 305 Sprints - Winged, Stock Cars, A Modifieds, Limited Sport Mod | Results | | Connor Masoner (Stock Cars) | - | 4th | - | 13th |
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