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| 5/6/2023 | Coles County Speedway - Mattoon, IL Non Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Adult Open, HART Non-Wing Micros | Results | | Caden Tolliver (Restricted 'A' Class) | 2nd | - | - | 2nd |
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| 5/20/2023 | Miami County Raceway - Peru, IN Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Senior Micros | Results | | Caden Tolliver (Restricted 'A' Class) | 2nd | - | - | 3rd |
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| 5/26/2023 | Macon Speedway - Macon, IL Cornfield Combat Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, HART Non-Wing Micros | Results | | Caden Tolliver (Restricted 'A' Class) | 3rd | - | - | 4th |
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| 5/27/2023 | Macon Speedway - Macon, IL Cornfield Combat with $5,000 to win Non Wing Micros Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, HART Non-Wing Micros | Results | | Caden Tolliver (Restricted 'A' Class) | 7th (DNF) | - | - | DNS |
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| 6/9/2023 | Coles County Speedway - Mattoon, IL Eastern Illinois Weekend #1 Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Adult Open, HART Non-Wing Micros | Results | | Caden Tolliver (Restricted 'A' Class) | 1st | - | - | 2nd |
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| 6/10/2023 | US 24 Speedway - Logansport, IN POINT NIGHT #4 Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, HART Non-Wing Micros, Senior Micros | Results | | Caden Tolliver (Restricted 'A' Class) | 2nd | - | - | 2nd |
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| 6/14/2023 | Thunder Hill Speedway - Menomonie, WI Storm Series Race #2 (Points Race) Restricted 'A' Class, Stock Non-Wing, Junior Class, Rookie Class, 250 Winged Outlaw, Junior Sportsman Dirt Karts, Open Dirt Karts, Cage Jr. 206 A, Flat Jr. 2 Clone Heavy | Results | | Caden Tolliver (Restricted 'A' Class) | 1st | - | - | 1st |
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| 7/8/2023 | Mississippi Thunder Kart Track - Fountain City, WI Points Race #6 Winged Sprints, Restricted 'A' Class, 125cc Winged Micros, Junior Class, Junior Champ, Junior 1 Lites Dirt Karts, Junior 2 Lites Dirt Karts, Adult Heavy, Dirt Cage Kart Junior 1, Dirt Cage Kart Junior 2, Flat Adult Clone Heavy, 250 Winged Outlaw, LO 206 Dirt Karts, Open Dirt Karts, Junior Slingshots | Results | | Caden Tolliver (Restricted 'A' Class) | 1st | - | - | 1st |
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| 7/14/2023 | Coles County Speedway - Mattoon, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Adult Open, HART Non-Wing Micros | Results | | Caden Tolliver (Restricted 'A' Class) | 2nd | - | - | 7th (DNF) |
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| 7/15/2023 | Thunder Hill Speedway - Menomonie, WI Badger Midget Mayhem (1st Ever!) Badger Midgets: Badger Midget Auto Racing Association Restricted 'A' Class, Stock Non-Wing | Results | | Caden Tolliver (Restricted 'A' Class) | 1st | - | - | 1st |
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| 7/21/2023 | Coles County Speedway - Mattoon, IL Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Adult Open, HART Non-Wing Micros | Results | | Caden Tolliver (Restricted 'A' Class) | 1st | - | - | 3rd (DNF) |
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| 8/5/2023 | Wayne County Speedway - Wayne City, IL Faster Saturday Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Caden Tolliver (Restricted 'A' Class) | 4th | - | - | 6th |
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| 8/18/2023 | Doe Run Raceway - Doe Run, MO 30 lap spectator race $300 to win plus all regular classes. Stock Cars, Winged Outlaw, Restricted 'A' Class, B Modifieds, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Caden Tolliver (Restricted 'A' Class) | 5th | - | - | 6th |
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| 8/19/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Racing Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caden Tolliver (Restricted 'A' Class) | 1st | - | - | 9th (DNF) |
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| 9/9/2023 | US 24 Speedway - Logansport, IN POINT NIGHT #10 LIUNA NOW600 JR SPRINT $300 TO WIN, DOUG WRIGHT RACING NOW600 REST. $300 TO WIN NW Restricted Non Winged Micros, Winged A-Class, Stock Non-Wing, Junior Sprints, HART Non-Wing Micros, Senior Micros | Results | | Caden Tolliver (Restricted Non Winged Micros) | 4th | - | - | DNS |
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| 9/30/2023 | Thunder Hill Speedway - Menomonie, WI Harvest Hustle (2 Day Show) Restricted 'A' Class, Winged A-Class, Junior Class, Rookie Class, 600cc Modifieds, 250 Winged Outlaw, Junior Sportsman Dirt Karts, Super Slingshots, Cage Jr. 206 A | Results | | Caden Tolliver (Restricted 'A' Class) | 4th | - | - | DNS |
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| 10/7/2023 | US 24 Speedway - Logansport, IN POINT NIGHT #12 FINAL POINT NIGHT OF 2023 SEASON Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, HART Non-Wing Micros, Senior Micros | Results | | Caden Tolliver (Restricted 'A' Class) | 8th | - | - | DNS |
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