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| 4/21/2023 | Viola Boyz Backroads Speedway - Viola, IL Season Opener Points Race Begins Junior 1 Lites Dirt Karts, Junior 2 Lites Dirt Karts, Rookie Class, Dirt Cage Kart Junior 1, Dirt Cage Kart Junior 2, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw, 500 Winged Open Outlaw, Kid Karts Dirt, Clone Lite Dirt Karts, Pro Stock Semi, Predator Maxxis | Results | | Ian Steward (250 Winged Outlaw) | 1st | - | - | 1st | | Ian Steward (500 Winged Open Outlaw) | 4th (DNF) | - | - | 5th |
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| 5/12/2023 | Viola Boyz Backroads Speedway - Viola, IL Points Race Junior 1 Lites Dirt Karts, Junior 2 Lites Dirt Karts, Rookie Class, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw, 500 Winged Open Outlaw, Kid Karts Dirt, Clone Lite Dirt Karts, Pro Stock Semi, Predator Maxxis | Results | | Ian Steward (250 Winged Outlaw) | 5th (DNF) | - | - | DNS | | Ian Steward (500 Winged Open Outlaw) | 4th (DNF) | - | - | DNS |
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| 5/20/2023 | Sebastian Speedway - Gladstone, IL Points Race Rookie Class, Cage Jr. 1 Clone, Flat Adult Clone, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw, 500 Winged Open Outlaw, 125 Winged Outlaw, Flat Jr. 2 Clone Heavy, Flat Jr. 1 Clone, Predator Hoosier | Results | | Ian Steward (250 Winged Outlaw) | 5th (DNF) | - | - | 3rd |
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| 5/27/2023 | Sebastian Speedway - Gladstone, IL Race Rookie Class, Cage Jr. 1 Clone, Flat Adult Clone, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw, 500 Winged Open Outlaw, 125 Winged Outlaw, Flat Jr. 2 Clone Heavy, Flat Jr. 1 Clone, Predator Hoosier | Results | | Ian Steward (250 Winged Outlaw) | 2nd | - | - | 6th (DNF) |
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| 6/3/2023 | Sebastian Speedway - Gladstone, IL Points Race Rookie Class, Cage Jr. 1 Clone, Flat Adult Clone, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw, 500 Winged Open Outlaw, 125 Winged Outlaw, Flat Jr. 2 Clone Heavy, Flat Jr. 1 Clone, Predator Hoosier | Results | | Ian Steward (250 Winged Outlaw) | 2nd | - | - | 1st |
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| 6/9/2023 | Viola Boyz Backroads Speedway - Viola, IL Mid-Season Championship Junior 1 Lites Dirt Karts, Junior 2 Lites Dirt Karts, Rookie Class, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw, 500 Winged Open Outlaw, Kid Karts Dirt, Clone Lite Dirt Karts, Pro Stock Semi, Predator Maxxis | Results | | Ian Steward (250 Winged Outlaw) | 4th | - | - | 2nd |
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| 6/16/2023 | English Creek Speedway - Knoxville, IA Points Race #6 Winged Outlaw, Adult Heavy, Adult Medium, Dirt Cage Kart Junior 1, Dirt Cage Kart Junior 2, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Ian Steward (Adult Heavy) | 3rd | - | - | 3rd |
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| 6/17/2023 | Sebastian Speedway - Gladstone, IL Race Rookie Class, Cage Jr. 1 Clone, Flat Adult Clone, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw, 500 Winged Open Outlaw, 125 Winged Outlaw, Flat Jr. 2 Clone Heavy, Flat Jr. 1 Clone, Predator Hoosier | Results | | Ian Steward (250 Winged Outlaw) | 2nd | - | - | 2nd (DNF) |
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| 7/3/2023 | Viola Boyz Backroads Speedway - Viola, IL Firecracker Special Junior 1 Lites Dirt Karts, Junior 2 Lites Dirt Karts, Rookie Class, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw, 500 Winged Open Outlaw, Kid Karts Dirt, Clone Heavy Dirt Karts, Clone Lite Dirt Karts, Predator Maxxis | Results | | Ian Steward (250 Winged Outlaw) | 2nd | - | - | 2nd |
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| 7/8/2023 | Sebastian Speedway - Gladstone, IL Points Race Rookie Class, Cage Jr. 1 Clone, Flat Adult Clone, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw, 500 Winged Open Outlaw, 125 Winged Outlaw, Flat Jr. 2 Clone Heavy, Flat Jr. 1 Clone, Predator Hoosier | Results | | Ian Steward (250 Winged Outlaw) | 2nd | - | - | 2nd |
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| 7/15/2023 | Sebastian Speedway - Gladstone, IL Race Rookie Class, Cage Jr. 1 Clone, Flat Adult Clone, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw, 500 Winged Open Outlaw, 125 Winged Outlaw, Flat Jr. 2 Clone Heavy, Flat Jr. 1 Clone, Predator Hoosier | Results | | Ian Steward (250 Winged Outlaw) | 1st | - | - | DNS |
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| 7/21/2023 | English Creek Speedway - Knoxville, IA Points Race #9 Winged Outlaw, Adult Heavy, Adult Medium, Dirt Cage Kart Junior 1, Dirt Cage Kart Junior 2, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Ian Steward (Adult Heavy) | 3rd | - | - | 2nd |
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| 7/29/2023 | Sebastian Speedway - Gladstone, IL Race Rookie Class, Cage Jr. 1 Clone, Flat Adult Clone, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw, 500 Winged Open Outlaw, 125 Winged Outlaw, Flat Jr. 2 Clone Heavy, Flat Jr. 1 Clone, Predator Hoosier | Results | | Ian Steward (250 Winged Outlaw) | 2nd | - | - | 4th |
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| 8/4/2023 | Sebastian Speedway - Gladstone, IL Happy Rock Summer Wing Kart Rumble Junior Champ, Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw, 500 Winged Open Outlaw, 125 Winged Outlaw | Results | | Ian Steward (250 Winged Outlaw) | 2nd | - | - | 13th (DNF) | | Ian Steward (500 Winged Open Outlaw) | 5th | - | 6th | - |
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| 8/7/2023 | English Creek Speedway - Knoxville, IA 19th Annual Outlaw Dirt Kart Nationals Winged Outlaw, Adult Heavy, Adult Medium, Dirt Cage Kart Junior 1, Dirt Cage Kart Junior 2, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Ian Steward (Adult Heavy) | 3rd | - | - | - | | Ian Steward (500 Winged Open Outlaw) | 5th | - | - | - |
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| 8/8/2023 | English Creek Speedway - Knoxville, IA 19th Annual Outlaw Dirt Kart Nationals Winged Outlaw, Adult Heavy, Adult Medium, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw | Results | | Ian Steward (Adult Heavy) | - | - | - | 10th | | Ian Steward (500 Winged Open Outlaw) | - | - | 14th (DNF) | - |
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| 8/11/2023 | Viola Boyz Backroads Speedway - Viola, IL Backroad Summer Nationals Junior Class, Junior 1 Lites Dirt Karts, Junior 2 Lites Dirt Karts, Rookie Class, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, Generic 1, 250 Winged Outlaw, 500 Winged Open Outlaw, Kid Karts Dirt, Clone Lite Dirt Karts, Pro Stock Semi, Predator Maxxis | Results | | Ian Steward (250 Winged Outlaw) | - | - | - | - |
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| 8/12/2023 | Viola Boyz Backroads Speedway - Viola, IL Backroad Summer Nationals Junior Class, Junior 1 Lites Dirt Karts, Junior 2 Lites Dirt Karts, Rookie Class, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, Generic 1, 250 Winged Outlaw, 500 Winged Open Outlaw, Kid Karts Dirt, Clone Lite Dirt Karts, Pro Stock Semi, Predator Maxxis | Results | | Ian Steward (250 Winged Outlaw) | 4th | - | - | 4th |
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| 8/26/2023 | Sebastian Speedway - Gladstone, IL Race Junior Champ, Rookie Class, Cage Jr. 1 Clone, Flat Adult Clone, Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw, 500 Winged Open Outlaw, Flat Jr. 2 Clone Heavy, Flat Jr. 1 Clone, Predator Hoosier | Results | | Ian Steward (500 Winged Open Outlaw) | 3rd | - | - | 3rd |
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