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| 5/23/2020 | Lee County Speedway - Donnellson, IA Return to Racing 305 Sprints - Winged, Midgets, A Modifieds, Street Stocks, Dirt Late Models | Results | | Will Armitage (Midgets) | 2nd | - | - | 2nd |
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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 | | Will Armitage (Economy Midgets) | 8th (DNF) | - | - | 10th |
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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 | | Will Armitage (Winged A-Class) | 5th | - | - | 13th |
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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 | | Will Armitage (Economy Midgets) | 1st | - | - | 1st |
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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 | | Will Armitage (Economy Midgets) | 2nd | - | - | 4th |
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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 | | Will Armitage (Midgets) | 7th | - | - | 11th |
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| 7/10/2020 | Lincoln Speedway - Lincoln, IL Weekly Racing Program Economy Midgets, DIRTcar UMP Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Will Armitage (Economy Midgets) | 2nd | - | - | 4th |
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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 | | Will Armitage (Winged A-Class) | 2nd | - | - | 3rd |
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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 | | Will Armitage (Economy Midgets) | 3rd | - | - | 7th |
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| 8/2/2020 | East Moline Speedway - East Moline, IL Greg Durbin Memorial Midgets, Street Stocks, IMCA Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock, Mod Lites | Results | | Will Armitage (Midgets) | 2nd | - | - | 3rd |
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| 8/7/2020 | Coles County Speedway - Mattoon, IL HART Series Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Will Armitage (Non-Wing Outlaw) | 6th | - | 2nd | 14th (DNF) |
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| 8/21/2020 | Lincoln Speedway - Lincoln, IL NIght Before State Fair Race Midgets: POWRi Economy Midgets, DIRTcar UMP Modifieds, Winged Outlaw, Pro Late Model | Results | | Will Armitage (Economy Midgets) | 3rd | - | - | 4th | | Will Armitage (Winged Outlaw) | 9th | - | - | 17th |
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| 8/29/2020 | Macon Speedway - Macon, IL Skeff Distributing Presents IMRA Midgets and Hornet World Championship / CEFCU Kid's Club Midgets, DIRTcar UMP Modifieds, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Will Armitage (Midgets) | 4th | - | - | 7th |
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| 9/4/2020 | Lincoln Speedway - Lincoln, IL Brandt Season Championships / $10 Admission with Food and Drink Specials Economy Midgets, DIRTcar UMP Modifieds, Sportsmans, Street Stocks, Hornets, Pro Late Model | Results | | Will Armitage (Economy Midgets) | 2nd | - | - | 8th (DNF) |
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| 9/13/2020 | Macon Speedway - Macon, IL 75th Season of Racing Celebration presented by Decatur Area Convention & Visitors Bureau DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Will Armitage (Winged A-Class) | 8th | - | - | 7th |
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| 9/26/2020 | Sycamore Speedway - Sycamore, IL Badger Midgets: Badger Midget Auto Racing Association | Results | | Will Armitage (Badger Midgets) | 4th | - | - | 6th |
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| 10/3/2020 | Miami County Raceway - Peru, IN FALL 40's - USAC Regional Midgets and NOW600 Non-Wing Micros Midgets, Winged A-Class, Hybrid 600cc Micros | Results | | Will Armitage (Midgets) | 5th | - | 1st | 18th |
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| 10/11/2020 | East Moline Speedway - East Moline, IL Harvest Havoc - Day 2 - Cheaters Night Midgets, Street Stocks, Vintage Full Body Stock Cars, IMCA Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock, Mod Lites | Results | | Will Armitage (Midgets) | 2nd | - | - | 3rd |
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| 10/16/2020 | Kokomo Speedway - Kokomo, IN Kokomo KlashXIV 305 Sprints - Winged, Midgets, Hobby Stocks, 410 Sprints - Non-Winged | Results | | Will Armitage (Midgets) | - | - | - | - |
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| 11/7/2020 | Wayne County Speedway - Wayne City, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Will Armitage (Lightning Sprints) | 5th | - | - | 3rd |
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| 11/20/2020 | Wayne County Speedway - Wayne City, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Will Armitage (Lightning Sprints) | 1st | - | - | 4th |
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