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| 6/12/2020 | Lincoln Speedway - Lincoln, IL 2020 Season Opener Economy Midgets, DIRTcar UMP Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | 3rd | - | - | 12th |
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| 6/13/2020 | Macon Speedway - Macon, IL Illinois SPEED Week Midgets: POWRi DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | 2nd | - | - | 5th |
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| 6/19/2020 | Lincoln Speedway - Lincoln, IL Lincoln Speedway Race Week #2 305 Sprints - Winged, Economy Midgets, DIRTcar UMP Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | 5th | - | - | 4th |
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| 6/20/2020 | Macon Speedway - Macon, IL Macon Speedway Race Week #2 DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | - | - | - | - |
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| 6/26/2020 | Lincoln Speedway - Lincoln, IL Lincoln Speedway Race Week #3 305 Sprints - Winged, Economy Midgets, DIRTcar UMP Modifieds, Hornets, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | 1st | - | - | 4th |
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| 7/3/2020 | Lincoln Speedway - Lincoln, IL Midget Special with Fireworks Midgets, DIRTcar UMP Modifieds, Hornets, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | DNS | - | 3rd | 8th |
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| 7/4/2020 | Macon Speedway - Macon, IL Dynagraphics & 95Q Firecracker 40s - Pro Late Models and Topless Modifieds with FIREWORKS Midgets, DIRTcar UMP Modifieds, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | 4th | - | - | 8th |
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| 7/11/2020 | Macon Speedway - Macon, IL Fireman's Ball & First Responders Night / Sportsman Topless 40 and CEFCU Kids Club DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | - | - | - | 7th |
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| 7/17/2020 | Lincoln Speedway - Lincoln, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Economy Midgets, DIRTcar UMP Modifieds, Hornets, 600cc Modifieds, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | 4th | - | - | 8th (DNF) |
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| 7/25/2020 | Macon Speedway - Macon, IL 6th Annual KERBYSTRONG 100 (Pro Lates $2,000 Win, Modifieds $700 Win, and Sportsman $600 Win DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | 4th | - | - | 9th (DNF) |
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| 8/7/2020 | Farmer City Raceway - Farmer City, IL 6th Annual $1K Street Stock "What up Dog 40" + Full Show DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Hornets, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | 6th | - | - | 14th |
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| 8/14/2020 | Farmer City Raceway - Farmer City, IL Full Show + B-mods DIRTcar UMP Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | 6th | - | - | 15th (DNF) |
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| 8/15/2020 | Macon Speedway - Macon, IL Eve of Destruction VI with FIREWORKS & Diane Bennett Memorial DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | 5th | - | - | 18th (DNF) |
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| 9/19/2020 | Macon Speedway - Macon, IL 98.1 GRIZ FM featuring Vintage Racing & Macon Speedway Hall of Fame Drivers Night DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Colby Sheppard (Pro Late Model) | 4th | - | - | 12th (DNF) |
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