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| 5/23/2021 | Monadnock Speedway - Winchester, NH Sunday Mudbog Mudslinger Dirt Mini Trucks, Super Truck, Dirt Pro Trucks, Drag Trophy, Drag Junior, Drag Open Air | Results | | Matt O'Brien (Drag Trophy) | - | - | - | 1st |
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| 6/20/2021 | Monadnock Speedway - Winchester, NH Sunday Mudbog Mudslinger Dirt Mini Trucks, Super Truck, Dirt Pro Trucks, Drag Trophy, Drag Junior, Drag Open Air | Results | | Matt O'Brien (Drag Trophy) | - | - | - | - |
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| 8/29/2021 | Monadnock Speedway - Winchester, NH The Whitcomb 125 Present by Milton Cat Dirt Mini Trucks, Asphalt Small Block Modifieds, Super Truck, Dirt Pro Trucks, Drag Trophy, Drag Junior, Drag Open Air | Results | | Matt O'Brien (Drag Trophy) | - | - | - | 1st | | Matt O'Brien (Drag Open Air) | - | - | - | 1st |
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| 9/4/2021 | Oswego Speedway - Oswego, NY 65th Annual CLASSIC WEEK - Classic Saturday Sprint Cars, Winged A-Class, Asphalt Small Block Modifieds, Sport Compact | Results | | Matt O'Brien (Winged A-Class) | 1st | - | - | - |
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| 9/12/2021 | Monadnock Speedway - Winchester, NH Sunday MudBog Mudslinger Dirt Mini Trucks, Super Truck, Dirt Pro Trucks, Drag Trophy, Drag Junior, Drag Open Air | Results | | Matt O'Brien (Drag Trophy) | - | - | - | 1st | | Matt O'Brien (Drag Open Air) | - | - | - | 1st |
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| 10/17/2021 | Monadnock Speedway - Winchester, NH Sunday Mudbog Mudslinger Dirt Mini Trucks, Super Truck, Dirt Pro Trucks, Drag Trophy, Drag Junior, Drag Open Air | Results | | Matt O'Brien (Drag Trophy) | - | - | - | 1st | | Matt O'Brien (Drag Open Air) | - | - | - | 1st |
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