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| 2/27/2021 | Tri City Speedway - Granite City, IL "Clash at the Coliseum" Indoor Winter Series Race #5 -Saturday @ the National Equestrian Center Winged Outlaw, Rookie Class, Junior 2 Animal Dirt Karts, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 500 Winged Open Outlaw, Kid Karts Dirt, Clone Heavy Dirt Karts, Clone Medium Dirt Karts, Clone Super Heavy Dirt Karts, Cage Jr. Predator, LO 206 Cage Junior 1 Winged, Flat Jr. 1 Clone, Predator Maxxis | Results | | Drake Timmerman (Predator Maxxis) | 6th | - | - | 10th |
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| 2/28/2021 | Tri City Speedway - Granite City, IL "Clash at the Coliseum" Indoor Winter Series Race #5 -Sunday @ the National Equestrian Center Winged Outlaw, Rookie Class, Junior 2 Animal Dirt Karts, Restricted Box Stock, Unrestricted Box Stock, Junior Honda, 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 | | Drake Timmerman (Predator Maxxis) | 5th | - | - | 6th |
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| 5/14/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #4 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Drake Timmerman (500 Winged Open Outlaw) | 5th | - | - | - |
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| 5/30/2021 | Poplar Grove Speedway - Kamrar, IA Memorial Day Race-Track Points Race Junior Class, Junior Champ, Winged Outlaw, Adult Open, Rookie Class, Dirt Cage Kart Junior 1, Dirt Cage Kart Junior 2, Junior Kohler Cage, Cage Jr. 2 Clone, Flat Adult Clone, Unrestricted Box Stock, 125 Yamaha, Flat RWYB, Flat Adult Clone Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw, Cage Jr. Sprints, Kid Karts Dirt, LO 206 Dirt Karts, Asphalt Sprint - LO206 Junior, Cage Sr. Predator, LO 206 Cage Adult Winged, LO 206 Cage Cadet Winged, Flat Jr. 1 Clone Heavy, Flat Jr. 2 Clone Heavy, Predator Maxxis, Predator Hoosier | Results | | Drake Timmerman (500 Winged Open Outlaw) | 1st | - | - | - |
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| 7/2/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #8 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Drake Timmerman (500 Winged Open Outlaw) | 5th | - | 6th (DNF) | - |
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| 7/16/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #9 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Drake Timmerman (500 Winged Open Outlaw) | 7th | - | - | 8th |
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| 7/18/2021 | Avcom Park Speedway - Avon, IL Season Opener - Kids Day Non-Wing Outlaw, Dirt Cage Kart Junior 1, Flat Adult Clone, Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw, 500 Winged Open Outlaw, Pony Stock, Flat Jr. 1 Clone, Predator Maxxis | Rain Out |
| 7/23/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #10 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Drake Timmerman (500 Winged Open Outlaw) | DNS | - | - | 8th (DNF) |
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| 7/30/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #11 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Rain Out |
| 8/7/2021 | Mississippi Thunder Kart Track - Fountain City, WI Battle of the Wings Winged Sprints, 125cc Winged Micros, Junior 1 Lites Dirt Karts, Junior 2 Lites Dirt Karts, Dirt Cage Kart Junior 1, Flat Adult Clone Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw, LO 206 Dirt Karts, Junior Slingshots | Rain Out |
| 8/9/2021 | English Creek Speedway - Knoxville, IA 2021 OUTLAW DIRT KART NATIONALS Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Drake Timmerman (500 Winged Open Outlaw) | 5th | - | - | - |
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| 8/10/2021 | English Creek Speedway - Knoxville, IA 2021 OUTLAW DIRT KART NATIONALS Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Drake Timmerman (500 Winged Open Outlaw) | - | - | 5th | 13th (DNF) |
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| 8/15/2021 | Tri City Speedway - Granite City, IL Sunday Racing DIRTcar Sport Compact, Winged Outlaw, Winged Outlaw, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw, Dirt Mini Late Models, LO 206 Cage Junior 1 Winged, Flat Jr. 1 Clone | Results | | Drake Timmerman (Winged Outlaw) | 6th | - | - | 8th |
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| 8/21/2021 | English Creek Speedway - Knoxville, IA POINTS RACE #12 Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Drake Timmerman (500 Winged Open Outlaw) | 4th | - | - | 5th |
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