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| 2/1/2020 | Tri City Speedway - Granite City, IL Clash at the Coliseum Weekend 3 Winged Outlaw, Junior 2 Animal Dirt Karts, Flat RWYB, 500 Winged Open Outlaw, Clone Heavy Dirt Karts, Clone Medium Dirt Karts, Clone Super Heavy Dirt Karts, LO 206 Cage Adult Winged, LO 206 Cage Junior 1 Winged, Flat Jr. 1 Clone, Predator Maxxis, Predator Hoosier | Results | | Chad Woolley (Winged Outlaw) | 4th | - | - | 9th |
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| 10/10/2020 | English Creek Speedway - Knoxville, IA Championship Night Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Chad Woolley (500 Winged Open Outlaw) | 4th | - | - | 4th |
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| 12/12/2020 | Tri City Speedway - Granite City, IL "Clash at the Coliseum" Indoor Winter Series Race #1 -Saturday @ the National Equestrian Center Winged Outlaw, Rookie Class, Junior 2 Animal Dirt Karts, Junior Honda, Junior Animal, Senior Honda, Light 160, Flat RWYB, 500 Winged Open Outlaw, Kid Karts Dirt, Clone Heavy Dirt Karts, Clone Medium Dirt Karts, Clone Super Heavy Dirt Karts, Red Rookie, Cage Jr. Predator, LO 206 Cage Junior 1 Winged, Flat Jr. 1 Clone, Predator Maxxis | Results | | Chad Woolley (Winged Outlaw) | 1st | - | - | 10th |
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| 12/13/2020 | Tri City Speedway - Granite City, IL "Clash at the Coliseum" Indoor Winter Series Race #1 -Sunday @ the National Equestrian Center Winged Outlaw, Rookie Class, Junior 2 Animal Dirt Karts, Junior Honda, Junior Animal, Senior Honda, Light 160, Flat RWYB, 500 Winged Open Outlaw, Kid Karts Dirt, Clone Heavy Dirt Karts, Clone Medium Dirt Karts, Clone Super Heavy Dirt Karts, Red Rookie, Cage Jr. Predator, LO 206 Cage Junior 1 Winged, Flat Jr. 1 Clone, Predator Maxxis | Results | | Chad Woolley (Winged Outlaw) | 3rd | - | - | 11th |
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