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| 5/15/2020 | Casper Speedway - Casper, WY Season Opener Hobby Stocks, Stock Cars, Dwarf, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Mod Four | Results | | Tripp Gaylord (IMCA Modified) | 1st | - | - | 6th |
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| 5/22/2020 | Sweetwater Speedway - Rock Springs, WY Rudy Yeager Memorial A Modifieds, B Modifieds, Street Stocks, Dwarf, 250 yamaha, Asphalt Street Stocks | Results | | Tripp Gaylord (A Modifieds) | 2nd | - | - | 23rd |
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| 5/23/2020 | Sweetwater Speedway - Rock Springs, WY Rudy Yeager Memorial A Modifieds, B Modifieds, Street Stocks, Dwarf, 250 yamaha, Asphalt Street Stocks | Results | | Tripp Gaylord (A Modifieds) | 2nd | - | - | 2nd |
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| 6/13/2020 | RPM Speedway - Hays, KS Nutrien Ag Solutions Mike Hughes Sunflower Classic Presented by Speed Shift TV Plus URSS Sprint Cars 305 Sprints - Winged, Generic 1, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tripp Gaylord (IMCA Modified) | 3rd | - | - | 22nd (DNF) | | Tripp Gaylord (IMCA Stock Car) | 2nd | - | - | 5th |
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| 6/14/2020 | RPM Speedway - Hays, KS Mike "Huey" Hughes Sunflower Classic Memorial Race Presented by Nutrien Ag Solutions 305 Sprints - Winged, Generic 1, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tripp Gaylord (IMCA Modified) | 4th | - | - | 8th | | Tripp Gaylord (IMCA Stock Car) | 7th | - | - | 18th (DNF) |
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| 6/19/2020 | Sweetwater Speedway - Rock Springs, WY Wild West Modified Tour A Modifieds, B Modifieds, Street Stocks, 250 yamaha, Asphalt Street Stocks | Results | | Tripp Gaylord (A Modifieds) | 1st | - | - | 1st | | Tripp Gaylord (Street Stocks) | 1st | - | - | 20th |
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| 6/20/2020 | Sweetwater Speedway - Rock Springs, WY Wild West Modified Tour A Modifieds, B Modifieds, Street Stocks, 250 yamaha, Asphalt Street Stocks | Results | | Tripp Gaylord (A Modifieds) | 1st | - | - | 2nd | | Tripp Gaylord (Street Stocks) | 7th | - | - | 23rd |
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| 7/10/2020 | Red River Valley Speedway - West Fargo, ND Dakota Classic Tour IMCA Modified: Dakota Classic Modified Tour IMCA Stock Car | Results | | Tripp Gaylord (IMCA Modified) | 1st | - | - | 6th | | Tripp Gaylord (IMCA Stock Car) | 2nd | - | - | 20th (DNF) |
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| 7/11/2020 | Jamestown Speedway - Jamestown, ND POWRi Minn-Kota Lightning Sprints at Jamestown Speedway Lightning Sprints: POWRi Minn-Kota Lightning Sprints IMCA Modified: Dakota Classic Modified Tour A Modifieds, B Modifieds, Street Stocks, Semi-Pro Legends, Winged Crate Sprints, Pure Stock, All Star Slingshots, IMCA Stock Car, WISSOTA Midwest Mods, WISSOTA Street Stock, Junior Slingshots | Results | | Tripp Gaylord (IMCA Modified) | 5th | - | 3rd | 27th (DNF) | | Tripp Gaylord (IMCA Stock Car) | 3rd | - | - | 7th |
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| 7/12/2020 | Nodak Speedway - Minot, ND Bullet Transmission Dakota Classic Modified Tour Night 3 IMCA Modified: Dakota Classic Modified Tour IMCA Stock Car | Results | | Tripp Gaylord (IMCA Modified) | 2nd | - | - | 16th | | Tripp Gaylord (IMCA Stock Car) | 3rd | - | - | 24th (DNF) |
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| 7/13/2020 | Williston Basin Speedway - Williston, ND Dakota Classic Modified Tour IMCA Modified: Dakota Classic Modified Tour A Modifieds, IMCA Stock Car | Results | | Tripp Gaylord (IMCA Modified) | 4th | - | 1st | 23rd (DNF) | | Tripp Gaylord (IMCA Stock Car) | 2nd | - | - | 24th (DNF) |
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| 7/14/2020 | Southwest Speedway - Dickinson, ND Dakota Classic Modified Tour IMCA Modified: Dakota Classic Modified Tour A Modifieds, IMCA Stock Car | Results | | Tripp Gaylord (IMCA Modified) | 2nd | - | - | 3rd | | Tripp Gaylord (IMCA Stock Car) | DNS | - | - | 14th (DNF) |
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| 7/15/2020 | Dacotah Speedway - Mandan, ND Dakota Classic Modified Tour IMCA Modified: Dakota Classic Modified Tour A Modifieds, IMCA Stock Car | Results | | Tripp Gaylord (IMCA Modified) | 1st | - | - | 1st |
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| 8/7/2020 | Park Jefferson International Speedway - Jefferson, SD 7th Annual J&J Fitting Iron Cup Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets, IMCA Modified | Results | | Tripp Gaylord (Stock Cars) | 4th | - | - | 12th (DNF) | | Tripp Gaylord (A Modifieds) | 1st | - | - | - |
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| 8/8/2020 | Park Jefferson International Speedway - Jefferson, SD 7th Annual J&J Fitting Iron Cup-IState Truck Centers Championship Night 305 Sprints - Winged, Hobby Stocks, Stock Cars, B Modifieds, Hornets, IMCA Modified | Results | | Tripp Gaylord (IMCA Modified) | - | - | - | 3rd |
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| 8/9/2020 | Dawson County Raceway - Lexington, NE Holbein Lawn Care and KLawn of Lexington Night! IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tripp Gaylord (IMCA Modified) | 2nd | - | - | 1st |
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| 8/21/2020 | Thomas County Speedway - Colby, KS 14th Annual Jeff Hartwell Memorial - Day 1 IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tripp Gaylord (IMCA Modified) | 1st | - | - | 1st |
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| 8/22/2020 | Thomas County Speedway - Colby, KS 14 Annual Jeff Hartwell Memorial - Day 2 IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tripp Gaylord (IMCA Modified) | 1st | - | - | 4th |
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| 9/4/2020 | Gillette Thunder Speedway - Gillette, WY 20th Annual East/West Clash Night 1 IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Tripp Gaylord (IMCA Modified) | 2nd | - | - | 5th |
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| 9/5/2020 | Gillette Thunder Speedway - Gillette, WY 20th Annual East/West Clash Night 2 IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Tripp Gaylord (IMCA Modified) | 1st | - | - | 1st |
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| 9/6/2020 | Gillette Thunder Speedway - Gillette, WY 20th Annual East/West Clash Championship Night IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Tripp Gaylord (IMCA Modified) | 1st | - | - | 1st |
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| 9/18/2020 | Sheridan Speedway - Sheridan, WY I 90 Challenge sponsored by First Northern Bank of Wyoming & Rocky Mountain Ambulance LLC Dirt Mini Trucks, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Tripp Gaylord (IMCA Modified) | 1st | - | - | 2nd |
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| 9/19/2020 | Sheridan Speedway - Sheridan, WY I 90 Challenge sponsored by First Northern Bank of Wyoming & Rocky Mountain Ambulance LLC Quarter Midgets, Dirt Mini Trucks, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Tripp Gaylord (IMCA Modified) | 1st | - | - | 1st |
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| 10/2/2020 | RPM Speedway - Hays, KS Briney Motorsports Fall Nationals, Presented by Nutrien Ag Solutions, Fueled by Casey's, Speedshift B Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tripp Gaylord (IMCA Modified) | 1st | - | - | - |
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| 10/3/2020 | RPM Speedway - Hays, KS Briney Motorsports Fall Nationals, Presented by Nutrien Ag Solutions, Fueled by Casey's, Speedshift B Modifieds, Generic 1, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Tripp Gaylord (IMCA Modified) | - | - | - | 3rd |
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| 11/11/2020 | Dirt Track at Las Vegas - Las Vegas, NV Duel in the Desert A Modifieds: Duel in the Desert Stock Cars, B Modifieds, IMCA Modified | Results | | Tripp Gaylord (A Modifieds) | 4th | - | 3rd | - |
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| 11/12/2020 | Dirt Track at Las Vegas - Las Vegas, NV Duel in the Desert A Modifieds: Duel in the Desert Stock Cars, B Modifieds, IMCA Modified | Results | | Tripp Gaylord (A Modifieds) | 1st | - | - | - |
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