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| 1/8/2021 | Heart Of Oklahoma Speedway - Shawnee, OK 4th Annual Outlaw Kart Superbowl Young Guns, Junior Champ, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Adult Heavy, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Cage Jr. 3 Clone, Flat RWYB, Flat Stock Flatheads Med, Flat Adult Clone Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Cage Jr. Sprints | Results | | Gage Montgomery (250 Winged Outlaw) | 8th (DNF) | - | - | - |
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| 1/9/2021 | Heart Of Oklahoma Speedway - Shawnee, OK 4th Annual Outlaw Kart Superbowl Young Guns, Junior Champ, Junior 1 Medium Dirt Karts, Junior 1 Heavy Dirt Karts, Adult Heavy, Cage Jr. 1 Clone, Cage Jr. 2 Clone, Flat Adult Clone, Cage Jr. 3 Clone, Flat RWYB, Flat Stock Flatheads Med, Flat Adult Clone Heavy, 250 Winged Outlaw, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, Cage Jr. Sprints | Results | | Gage Montgomery (250 Winged Outlaw) | 5th | - | 8th | - |
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| 1/10/2021 | Tri City Speedway - Granite City, IL "Clash at the Coliseum" Indoor Winter Series Race #2 -Sunday @ 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 | | Gage Montgomery (Winged Outlaw) | 4th | - | - | 5th | | Gage Montgomery (500 Winged Open Outlaw) | 4th | - | - | 1st |
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| 1/23/2021 | Tri City Speedway - Granite City, IL "Clash at the Coliseum" Indoor Winter Series Race #3 -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 | | Gage Montgomery (Winged Outlaw) | 1st | - | - | 2nd | | Gage Montgomery (500 Winged Open Outlaw) | 1st | - | - | 1st |
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| 1/24/2021 | Tri City Speedway - Granite City, IL "Clash at the Coliseum" Indoor Winter Series Race #3 -Sunday @ the National Equestrian Center Winged Outlaw, Rookie Class, Junior 2 Animal Dirt Karts, Restricted Box Stock, Unrestricted Box Stock, Junior Honda, Senior Honda, 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 | | Gage Montgomery (Winged Outlaw) | 5th | - | - | 5th | | Gage Montgomery (500 Winged Open Outlaw) | 3rd | - | - | 4th |
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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 | | Gage Montgomery (Winged Outlaw) | 2nd | - | - | 8th | | Gage Montgomery (500 Winged Open Outlaw) | 1st | - | - | 1st |
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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 | | Gage Montgomery (Winged Outlaw) | 2nd | - | - | DNS | | Gage Montgomery (500 Winged Open Outlaw) | 2nd | - | - | 5th |
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