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| 2/5/2021 | Hendry County Motorsports Park - Clewiston, FL USCS Snow Free Sprint Car Car Winter Nationals Round #1 360 Sprints - Winged: USCS United Sprint Car Series Hobby Stocks | Results | | Phil Gressman (360 Sprints - Winged) | 1st | - | - | 12th |
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| 2/6/2021 | Hendry County Motorsports Park - Clewiston, FL USCS Snow Free Sprint Car Car Winter Nationals Round #2 360 Sprints - Winged: USCS United Sprint Car Series Hobby Stocks | Results | | Phil Gressman (360 Sprints - Winged) | 7th | - | - | 15th |
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| 4/16/2021 | I-96 Speedway - Lake Odessa, MI Great Lakes Super Sprints - Ice Breaker 360 Sprints - Winged: GLSS-Great Lakes Super Sprints B Modifieds, Street Stocks, Mini Wedge, Mini Outlaws, Sport Compact | Results | | Phil Gressman (360 Sprints - Winged) | 1st | - | - | 5th |
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| 4/24/2021 | Wayne County Speedway - Orrville, OH 360 Sprints - Winged: GLSS-Great Lakes Super Sprints | Rain Out |
| 5/7/2021 | I-96 Speedway - Lake Odessa, MI 360 Sprints - Winged: ASCS National with GLSS-Great Lakes Super Sprints 410 Sprints - Non-Winged: Great Lakes Traditional Sprints with BOSS Buckeye Outlaw Sprint Series | Rain Out |
| 5/8/2021 | I-96 Speedway - Lake Odessa, MI 360 Sprints - Winged: ASCS National with GLSS-Great Lakes Super Sprints 410 Sprints - Non-Winged: Great Lakes Traditional Sprints with BOSS Buckeye Outlaw Sprint Series | Results | | Phil Gressman (360 Sprints - Winged) | 3rd | - | - | 22nd (DNF) |
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| 5/21/2021 | Tri-City Motor Speedway - Auburn, MI 360 Sprints - Winged: GLSS-Great Lakes Super Sprints Lightning Sprints: Great Lakes Lightning Sprints DIRTcar Late Models, Factory Stocks, Hobby Stocks, Mini Wedge, Mini Outlaws | Results | | Phil Gressman (360 Sprints - Winged) | 3rd | - | - | 11th |
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| 5/29/2021 | Crystal Motor Speedway - Crystal, MI 360 Sprints - Winged: GLSS-Great Lakes Super Sprints Hobby Stocks, A Modifieds, Street Stocks, Dirt Late Models, Dirt Pro Trucks, Mini Outlaws, Sport Compact | Results | | Phil Gressman (360 Sprints - Winged) | 1st | - | - | 7th |
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| 6/4/2021 | I-96 Speedway - Lake Odessa, MI Great Lakes Super Sprints 360 Sprints - Winged: GLSS-Great Lakes Super Sprints B Modifieds, Street Stocks, Mini Wedge, Mini Outlaws, Sport Compact | Results | | Phil Gressman (360 Sprints - Winged) | 5th | - | 2nd | 16th |
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| 6/5/2021 | Butler Speedway - Quincy, MI 360 Sprints - Winged: GLSS-Great Lakes Super Sprints 410 Sprints - Winged | Results | | Phil Gressman (360 Sprints - Winged) | 6th | - | 1st | 10th |
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| 7/2/2021 | I-96 Speedway - Lake Odessa, MI Great Lakes Super Sprints 360 Sprints - Winged: GLSS-Great Lakes Super Sprints B Modifieds, Street Stocks | Results | | Phil Gressman (360 Sprints - Winged) | 2nd | - | - | 5th |
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| 7/3/2021 | Crystal Motor Speedway - Crystal, MI 360 Sprints - Winged: GLSS-Great Lakes Super Sprints Hobby Stocks, A Modifieds, Street Stocks, Dirt Late Models, Junior 1 Lites Dirt Karts, Mini Wedge, Sport Compact | Results | | Phil Gressman (360 Sprints - Winged) | 2nd | - | - | 3rd |
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| 7/9/2021 | Hartford Speedway - Hartford, MI 360 Sprints - Winged: GLSS-Great Lakes Super Sprints 410 Sprints - Non-Winged: Great Lakes Traditional Sprints Hobby Stocks, Stock Cars | Results | | Phil Gressman (360 Sprints - Winged) | 3rd | - | - | 17th |
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| 7/10/2021 | Merritt Speedway - Merritt, MI 360 Sprints - Winged: GLSS-Great Lakes Super Sprints 410 Sprints - Non-Winged: Great Lakes Traditional Sprints Lightning Sprints: Great Lakes Lightning Sprints DIRTcar UMP Modifieds, Hobby Stocks, B Modifieds, Mini Wedge, Mini Outlaws | Results | | Phil Gressman (360 Sprints - Winged) | 3rd | - | - | 11th |
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| 7/30/2021 | I-96 Speedway - Lake Odessa, MI Wing Fling II 360 Sprints - Winged: GLSS-Great Lakes Super Sprints 410 Sprints - Winged: FASTonDIRT with SOD-Sprints On Dirt (410s) Street Stocks | Results | | Phil Gressman (360 Sprints - Winged) | 2nd | - | - | 7th |
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| 7/31/2021 | Fremont Speedway - Fremont, OH 360 Sprints - Winged: GLSS-Great Lakes Super Sprints 410 Sprints - Winged: FASTonDIRT | Results | | Phil Gressman (360 Sprints - Winged) | 3rd | - | - | 8th |
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| 8/6/2021 | Tri-City Motor Speedway - Auburn, MI 360 Sprints - Winged: GLSS-Great Lakes Super Sprints 410 Sprints - Non-Winged: Great Lakes Traditional Sprints Lightning Sprints: Great Lakes Lightning Sprints | Results | | Phil Gressman (360 Sprints - Winged) | 1st | - | - | 8th |
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| 8/13/2021 | Hartford Speedway - Hartford, MI 360 Sprints - Winged: GLSS-Great Lakes Super Sprints DIRTcar UMP Modifieds, Hobby Stocks, Stock Cars | Results | | Phil Gressman (360 Sprints - Winged) | 3rd | - | - | 8th |
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| 8/14/2021 | Thunderbird Raceway - Muskegon, MI 360 Sprints - Winged: GLSS-Great Lakes Super Sprints Factory Stocks, Stock Cars, A Modifieds, Pro Late Model, Mini Wedge, Mini Outlaws, Sport Compact | Results | | Phil Gressman (360 Sprints - Winged) | 2nd | - | - | 4th |
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| 9/3/2021 | I-96 Speedway - Lake Odessa, MI Great Lakes Sprint Showdown - Night 1 360 Sprints - Winged: GLSS-Great Lakes Super Sprints 410 Sprints - Non-Winged: Great Lakes Traditional Sprints Lightning Sprints: Great Lakes Lightning Sprints | Results | | Phil Gressman (360 Sprints - Winged) | 2nd | - | - | 5th |
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| 9/10/2021 | Tri-City Motor Speedway - Auburn, MI 360 Sprints - Winged: GLSS-Great Lakes Super Sprints 410 Sprints - Non-Winged: Great Lakes Traditional Sprints Lightning Sprints: Great Lakes Lightning Sprints DIRTcar UMP Modifieds, B Modifieds | Results | | Phil Gressman (360 Sprints - Winged) | 4th | - | - | 5th |
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| 9/11/2021 | Merritt Speedway - Merritt, MI 360 Sprints - Winged: GLSS-Great Lakes Super Sprints 410 Sprints - Non-Winged: Great Lakes Traditional Sprints Lightning Sprints: Great Lakes Lightning Sprints DIRTcar UMP Modifieds, Hobby Stocks, B Modifieds | Results | | Phil Gressman (360 Sprints - Winged) | 2nd | - | - | 7th |
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| 9/18/2021 | Fremont Speedway - Fremont, OH 410 Sprints - Winged: FASTonDIRT 410 Sprints - Non-Winged: BOSS Buckeye Outlaw Sprint Series | Results | | Phil Gressman (410 Sprints - Winged) | 1st | - | - | 10th |
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| 9/24/2021 | Skyline Speedway - Stewart, OH 410 Sprints - Winged: OVSCA-Ohio Valley Sprint Car Association | Results | | Phil Gressman (410 Sprints - Winged) | - | 3rd | - | 5th |
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| 9/25/2021 | Fremont Speedway - Fremont, OH | Results | | Phil Gressman (410 Sprints - Winged) | 5th | - | - | 10th |
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| 10/8/2021 | Fremont Speedway - Fremont, OH Jim and Joanne Ford Classic $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Rain Out |
| 10/9/2021 | Fremont Speedway - Fremont, OH Jim and Joanne Ford Classic $10,000 to win 410 Sprints - Winged: All Star Circuit of Champions Sprint Cars | Results | | Phil Gressman (410 Sprints - Winged) | 1st | 5th | - | 22nd (DNF) |
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