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| 4/20/2019 | Macon Speedway - Macon, IL Dollar Dog / $2.00 Beer Night & Spectator Drags DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Will Armitage (Winged A-Class) | 7th | - | - | 16th (DNF) |
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| 5/27/2019 | Macon Speedway - Macon, IL Mueller Dist. Miller Lite Twin 50s (Super Late Models and Pro Mods) & City of Macon Night DIRTcar Late Models, DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets | Results | | Will Armitage (Winged A-Class) | 1st | - | - | 19th (DNF) |
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| 7/6/2019 | Macon Speedway - Macon, IL Dean Garland Classic Street Stocks: Midwest Stock Car Tour DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Hornets, Pro Late Model | Results | | Will Armitage (Winged A-Class) | 5th | - | - | 11th (DNF) |
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| 7/13/2019 | Macon Speedway - Macon, IL Miles Chevrolet & Fireman's Ball and First Responders Night DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Will Armitage (Winged A-Class) | 7th (DNF) | - | - | 8th |
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| 7/27/2019 | Macon Speedway - Macon, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets with POWRi Winged A-Class, B Modifieds, Pro Late Model | Results | | Will Armitage (Winged A-Class) | 3rd | - | - | 4th |
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| 8/10/2019 | Macon Speedway - Macon, IL Eve of Destruction IV / Fireworks featuring Diane Bennett Memorial Rollover Contest DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Will Armitage (Winged A-Class) | 3rd | - | - | 5th |
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| 8/30/2019 | Lincoln Speedway - Lincoln, IL Brandt Season Championships FIVE BUCK Night (Grandstand Admissions) Economy Midgets, DIRTcar UMP Modifieds, Sportsmans, Street Stocks, Hornets, Pro Late Model | Results | | Will Armitage (Economy Midgets) | 3rd | - | - | 5th |
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| 8/31/2019 | Peoria Speedway - Peoria, IL Midgets, DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks, Hornets | Results | | Will Armitage (Midgets) | 4th | - | - | - |
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| 9/1/2019 | Wayne County Speedway - Wayne City, IL HART Non-Wing Sprints at Jacksonville Speedway Non-Wing Outlaw | Results | | Will Armitage (Non-Wing Outlaw) | DNS | - | - | 4th |
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| 9/6/2019 | Jacksonville Speedway - Jacksonville, IL Herb Barlow Memorial 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets Winged Outlaw | Results | | Will Armitage (Winged Outlaw) | 4th | - | - | 11th |
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| 9/14/2019 | Lee County Speedway - Donnellson, IA Non-Winged Sprints: Iowa Sprint Car League 305 Sprints - Winged, Economy Midgets, A Modifieds, B Modifieds | Results | | Will Armitage (Economy Midgets) | 7th | - | - | 10th |
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| 10/19/2019 | Peoria Speedway - Peoria, IL Midgets, DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Hornets | Results | | Will Armitage (Midgets) | 2nd | - | - | 3rd |
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| 11/2/2019 | 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 | - | - | 3rd |
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