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| 3/13/2021 | Wayne County Speedway - Wayne City, IL DuQuoin Winter Nationals - Week 3 - Night 2 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Kyle Barker (Winged Outlaw) | 9th | - | - | 14th |
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| 5/1/2021 | Macon Speedway - Macon, IL CEFCU Kid's Club Regular Night of Racing DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Kyle Barker (Winged A-Class) | 5th | - | - | 15th |
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| 5/15/2021 | Macon Speedway - Macon, IL 95Q Armed Forces Night (Featuring Free Admission for Active and Retired Military DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Kyle Barker (Winged A-Class) | 3rd | - | - | 3rd |
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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 | | Kyle Barker (Winged Outlaw) | 9th | - | - | 10th |
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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 | | Kyle Barker (Winged Outlaw) | 4th | - | - | 18th |
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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 | | Kyle Barker (Winged A-Class) | 5th | - | - | 9th |
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| 6/12/2021 | Macon Speedway - Macon, IL Taylorville Night Featuring Power Wheels emo Derby & CEFCU Kids DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Kyle Barker (Winged A-Class) | 3rd | - | - | 10th |
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| 6/16/2021 | Charleston Speedway - Charleston, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Kyle Barker (Winged Outlaw) | 2nd | - | - | 6th |
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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 | | Kyle Barker (Winged Outlaw) | 4th | - | - | 7th |
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| 6/18/2021 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Kyle Barker (Winged Outlaw) | 5th | - | - | 12th |
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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 | | Kyle Barker (Winged Outlaw) | 1st | - | - | 1st | | Kyle Barker (Winged A-Class) | - | - | - | 1st |
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| 7/2/2021 | Sweet Springs Motorsports Complex - Sweet Springs, MO Small Town Throwdown Winged Outlaw | Results | | Kyle Barker (Winged Outlaw) | - | - | - | - |
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| 7/2/2021 | US 24 Speedway - Logansport, IN Hart Series Outlaw NW $500 to win $75 to start Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Senior Micros | Results | | Kyle Barker (Non-Wing Outlaw) | 6th | - | 11th | - |
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| 7/3/2021 | Macon Speedway - Macon, IL Dynagraphics/95Q Firecracker 40s Pro Late Model/Topless Modified (Fireworks) DIRTcar UMP Modifieds, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Kyle Barker (Winged A-Class) | 5th | - | - | 7th |
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| 7/17/2021 | Macon Speedway - Macon, IL Church Night Featuring Faster Pastor Race DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model, Limited Modified | Results | | Kyle Barker (Winged A-Class) | 4th | - | - | 5th |
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| 7/22/2021 | Wayne County Speedway - Wayne City, IL Hart Non-Wing Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Kyle Barker (Winged Outlaw) | 1st | - | - | 4th |
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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 | | Kyle Barker (Winged Outlaw) | 5th | - | - | 8th |
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| 8/7/2021 | Macon Speedway - Macon, IL Diane Bennett Memorial DIRTcar UMP Modifieds, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Kyle Barker (Winged A-Class) | 3rd | - | - | 5th |
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| 8/14/2021 | Macon Speedway - Macon, IL HART Non Wing Micros DIRTcar UMP Modifieds, Non-Wing Outlaw, Stock Non-Wing, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Kyle Barker (Non-Wing Outlaw) | 2nd | - | - | 7th |
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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 | | Kyle Barker (Non-Wing Outlaw) | 2nd | - | - | 7th |
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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 | | Kyle Barker (Winged Outlaw) | 4th | - | - | 7th |
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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 | | Kyle Barker (Winged Outlaw) | 4th | - | 4th | - |
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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 | | Kyle Barker (Winged Outlaw) | 7th | - | 9th | - |
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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 | | Kyle Barker (Winged Outlaw) | 3rd | - | - | 12th |
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| 9/11/2021 | Macon Speedway - Macon, IL 98.1 Griz FM night featuring Vintage Racing of Ilinois Macon Speedway Hall of Fame Drivers DIRTcar UMP Modifieds, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Kyle Barker (Winged A-Class) | 2nd | - | - | 3rd |
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