| | Heat | Dash | B Feature | A Feature |
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| 1/14/2020 | Tulsa Expo Raceway - Tulsa, OK Warren CAT Qualifying Night Midgets: Chili Bowl Nationals | Results | | Jesse Colwell (Midgets) | - | - | - | - |
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| 1/15/2020 | Tulsa Expo Raceway - Tulsa, OK Hard Rock Casino Qualifying Night Midgets: Chili Bowl Nationals | Results | | Jesse Colwell (Midgets) | 1st | 4th | 1st | 15th |
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| 1/18/2020 | Tulsa Expo Raceway - Tulsa, OK Lucas Oil Championship Night Midgets: Chili Bowl Nationals | Results | | Jesse Colwell (Midgets) | - | - | - | - |
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| 2/1/2020 | Red Bluff Outlaws - Red Bluff, CA Points Race #8 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Open Dirt Karts | Results | | Jesse Colwell (500 Winged Open Outlaw) | 4th | 2nd | 1st | 10th |
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| 2/7/2020 | Ocala Speedway - Ocala, FL Winter Dirt Games XI Midgets: USAC National Midgets Stock Cars | Results | | Jesse Colwell (Midgets) | 4th | - | - | 20th |
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| 2/8/2020 | Ocala Speedway - Ocala, FL Winter Dirt Games XI Midgets: USAC National Midgets Stock Cars | Results | | Jesse Colwell (Midgets) | 3rd | - | - | 9th |
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| 2/15/2020 | Red Bluff Outlaws - Red Bluff, CA Points Race #10 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Open Dirt Karts | Results | | Jesse Colwell (500 Winged Open Outlaw) | 3rd | - | 5th | 10th |
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| 3/7/2020 | Red Bluff Outlaws - Red Bluff, CA Points Race #11 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Open Dirt Karts | Results | | Jesse Colwell (500 Winged Open Outlaw) | 1st | 1st | - | 7th |
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| 3/14/2020 | Red Bluff Outlaws - Red Bluff, CA Points Race #12 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Open Dirt Karts | Results | | Jesse Colwell (500 Winged Open Outlaw) | 1st | - | - | 3rd |
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| 10/23/2020 | Red Bluff Outlaws - Red Bluff, CA Burris Bullring Showdown - (Night #1) Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Open Dirt Karts | Results | | Jesse Colwell (500 Winged Open Outlaw) | 8th (DNF) | - | - | - |
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| 10/24/2020 | Red Bluff Outlaws - Red Bluff, CA Burris Bullring Showdown - (Night #2) Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Open Dirt Karts | Results | | Jesse Colwell (500 Winged Open Outlaw) | 6th | - | 1st | 14th (DNF) |
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| 10/31/2020 | Red Bluff Outlaws - Red Bluff, CA Points Race #1 - (Tyler Wolf Memorial) Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Open Dirt Karts | Results | | Jesse Colwell (500 Winged Open Outlaw) | 1st | - | - | 15th (DNF) |
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| 11/7/2020 | Red Bluff Outlaws - Red Bluff, CA Points Race #2 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Open Dirt Karts | Results | | Jesse Colwell (500 Winged Open Outlaw) | 4th | - | 16th | - |
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