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| 1/1/2021 | Tulsa Expo Raceway - Tulsa, OK Racing Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Trevin Littleton (Restricted 'A' Class) | - | 5th | - | - | | Trevin Littleton (Winged A-Class) | - | 10th | - | - |
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| 1/2/2021 | Tulsa Expo Raceway - Tulsa, OK Driller Time! Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Trevin Littleton (Winged Outlaw) | - | - | - | - | | Trevin Littleton (Restricted 'A' Class) | - | - | - | - | | Trevin Littleton (Winged A-Class) | - | - | - | - |
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| 3/26/2021 | I-44 Riverside Speedway - Oklahoma City, OK Turnpike Challenge Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw, Stock Non-Wing | Results | | Trevin Littleton (Winged Outlaw) | 5th | - | 8th | - |
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| 3/27/2021 | I-44 Riverside Speedway - Oklahoma City, OK Turnpike Challenge Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw, Winged A-Class | Results | | Trevin Littleton (Winged Outlaw) | 8th | - | 11th | 16th |
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| 3/28/2021 | Port City Raceway - Tulsa, OK Turnpike Challenge Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw | Results | | Trevin Littleton (Winged Outlaw) | 5th | - | 3rd | 22nd |
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| 4/30/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race (1) Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Trevin Littleton (Winged Outlaw) | 3rd | - | - | 3rd |
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| 5/1/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race (2) Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Trevin Littleton (Winged Outlaw) | 5th | - | - | 3rd |
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| 5/7/2021 | Coles County Speedway - Mattoon, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Trevin Littleton (Winged Outlaw) | 1st | - | - | 2nd |
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| 5/21/2021 | Charleston Speedway - Charleston, IL ILLIANA Showdown Midgets: POWRi National Midgets with POWRi Non-Winged Sprints: POWRi WAR Sprints Winged Outlaw | Results | | Trevin Littleton (Winged Outlaw) | 3rd | - | - | 5th |
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| 5/22/2021 | Charleston Speedway - Charleston, IL ILLIANA Showdown Midgets: POWRi National Midgets with POWRi Non-Winged Sprints: POWRi WAR Sprints Winged Outlaw | Results | | Trevin Littleton (Winged Outlaw) | 5th | - | - | 7th |
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| 5/31/2021 | Macon Speedway - Macon, IL Memorial Day Twin 50s - SLM 50 laps & Modifieds 50 laps DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets | Results | | Trevin Littleton (Winged A-Class) | 1st | - | - | 6th |
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| 6/4/2021 | Coles County Speedway - Mattoon, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Trevin Littleton (Winged Outlaw) | 1st | - | - | 2nd |
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| 6/5/2021 | Southern Illinois Raceway - Marion, IL Performance Electronics Prelude to the Hustle Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Trevin Littleton (Winged Outlaw) | 6th | - | 2nd | DNS |
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| 6/16/2021 | Charleston Speedway - Charleston, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Trevin Littleton (Winged Outlaw) | 4th | - | - | 5th |
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| 6/17/2021 | Lincoln Speedway - Lincoln, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi DIRTcar UMP Modifieds, Winged Outlaw, Pro Late Model | Results | | Trevin Littleton (Winged Outlaw) | 1st | - | - | 6th |
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| 6/18/2021 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Trevin Littleton (Winged Outlaw) | 4th | - | - | 6th |
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| 6/19/2021 | Macon Speedway - Macon, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw, Winged A-Class, Street Stocks, Pro Late Model | Results | | Trevin Littleton (Winged Outlaw) | 6th | - | - | 5th | | Trevin Littleton (Winged A-Class) | - | - | - | 5th |
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| 6/20/2021 | Brownstown Bullring - Brownstown, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Trevin Littleton (Winged Outlaw) | 6th | - | - | 12th |
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| 7/2/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Small Town Throwdown Winged Outlaw | Results | | Trevin Littleton (Winged Outlaw) | 3rd | - | - | 11th |
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| 7/3/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Small Town Throwdown Championship Night Winged Outlaw | Results | | Trevin Littleton (Winged Outlaw) | 3rd | - | 1st | 14th |
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| 7/10/2021 | US 24 Speedway - Logansport, IN Jr Sprint Clash 1st $300, 2nd $200, 3rd $100 Rest run NW point night 4 GREAT 8 Winged Outlaw, Non-Wing Outlaw, Restricted Non Winged Micros, Winged A-Class, Stock Non-Wing, Junior Sprints, Senior Micros | Results | | Trevin Littleton (Winged Outlaw) | 5th | - | - | - |
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| 7/17/2021 | Southern Illinois Raceway - Marion, IL Ike Dealership JR Sprint Special/Rising Stars Night Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Trevin Littleton (Winged Outlaw) | 1st | - | - | 20th (DNF) |
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| 7/24/2021 | Southern Illinois Raceway - Marion, IL Points Night/HART Non-Wing Series Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Trevin Littleton (Winged Outlaw) | 3rd | - | - | 9th (DNF) |
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| 8/1/2021 | Avcom Park Speedway - Avon, IL Kid's Night Take 2 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. 2 Clone Heavy, Flat Jr. 1 Clone, Predator Maxxis | Results | | Trevin Littleton (Non-Wing Outlaw) | 1st | - | - | - |
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| 8/7/2021 | Wayne County Speedway - Wayne City, IL Hyper NON-Wing Outlaws $1250 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Trevin Littleton (Winged Outlaw) | 4th | - | - | 3rd |
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| 8/13/2021 | Coles County Speedway - Mattoon, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Trevin Littleton (Winged Outlaw) | 1st | - | - | 6th (DNF) | | Trevin Littleton (Non-Wing Outlaw) | 3rd | - | - | - |
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| 8/14/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race (16) Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Trevin Littleton (Winged Outlaw) | 3rd | - | - | 1st |
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| 8/15/2021 | Jacksonville Speedway - Jacksonville, IL Central Illinois' Non-Wing Swing Night #2 410 Sprints - Winged, Non-Wing Outlaw | Results | | Trevin Littleton (Non-Wing Outlaw) | 5th | - | - | 4th |
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| 8/20/2021 | Charleston Speedway - Charleston, IL POWRi at Charleston Speedway Midgets: POWRi National Midgets with POWRi Winged Outlaw, Hornets, DIRTcar Pro Modifieds | Results | | Trevin Littleton (Winged Outlaw) | 2nd | - | - | 4th |
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| 8/27/2021 | Wayne County Speedway - Wayne City, IL Showdown in Beantown Night #1 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Trevin Littleton (Winged Outlaw) | DNS | - | DNS | - |
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| 8/28/2021 | Wayne County Speedway - Wayne City, IL Showdown in Beantown Night #2 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Trevin Littleton (Winged Outlaw) | 3rd | - | - | 10th |
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| 9/10/2021 | Jacksonville Speedway - Jacksonville, IL Herb Barlow Memorial 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Trevin Littleton (Winged Outlaw) | 2nd | - | - | 1st |
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| 9/25/2021 | Wayne County Speedway - Wayne City, IL Dan Robinson Memorial Night #2 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Trevin Littleton (Winged Outlaw) | 2nd | - | - | 16th |
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| 10/1/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Sweet Springs Fall Brawl Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints | Results | | Trevin Littleton (Winged Outlaw) | 4th | - | - | 10th |
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| 10/2/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Sweet Springs Fall Brawl Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints | Results | | Trevin Littleton (Winged Outlaw) | 3rd | - | - | 2nd |
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| 10/9/2021 | Lake Ozark Speedway - Eldon, MO Lake Ozark Speedway Chase for the Championship Night 360 Sprints - Winged: ASCS Warrior Region 305 Sprints - Winged, Midwest Modifieds, Super Stocks, Pure Stock | Results | | Trevin Littleton (305 Sprints - Winged) | 3rd | - | - | 17th |
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| 10/14/2021 | Port City Raceway - Tulsa, OK Donnie Ray Crawford Sooner State 55 Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw | Results | | Trevin Littleton (Winged Outlaw) | 1st | - | - | 3rd |
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| 10/15/2021 | I-44 Riverside Speedway - Oklahoma City, OK Meents Memorial Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw, Stock Non-Wing | Results | | Trevin Littleton (Winged Outlaw) | 2nd | - | - | 6th |
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| 10/16/2021 | I-44 Riverside Speedway - Oklahoma City, OK Meents Memorial Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw, Winged A-Class | Results | | Trevin Littleton (Winged Outlaw) | 8th | - | - | 12th |
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| 10/23/2021 | Jacksonville Speedway - Jacksonville, IL | Results | | Trevin Littleton (410 Sprints - Winged) | 6th | - | - | 17th |
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| 11/5/2021 | Caney Valley Speedway - Caney, KS Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw, Pure Stock, USRA Tuners | Results | | Trevin Littleton (Winged Outlaw) | 2nd | - | - | 5th |
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| 11/6/2021 | Caney Valley Speedway - Caney, KS Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Factory Stocks, Winged Outlaw, USRA B-Mods | Results | | Trevin Littleton (Winged Outlaw) | 1st | - | - | 3rd |
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