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| 4/13/2019 | Macon Speedway - Macon, IL 74th Season Opener / Driver - Sponsor Appreciation Photos and Autographs DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Tommy Pickering (Street Stocks) | 3rd | - | - | 7th |
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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 | | Tommy Pickering (Street Stocks) | 4th | - | - | 12th (DNF) |
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| 5/18/2019 | Macon Speedway - Macon, IL Armed Forces Night / Featuring Free Admission for Active & Retired Military DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Tommy Pickering (Street Stocks) | 2nd | - | - | 11th (DNF) |
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| 5/24/2019 | Farmer City Raceway - Farmer City, IL A Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Tommy Pickering (Street Stocks) | 8th | - | - | 15th |
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| 6/7/2019 | Farmer City Raceway - Farmer City, IL A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Tommy Pickering (Street Stocks) | 8th | - | - | DNS |
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| 6/8/2019 | Macon Speedway - Macon, IL Caterpillar & Pabst Blue Ribbon Diesel Truck & Little League Night / $1,000 to Win Hornet Challenge DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Tommy Pickering (Street Stocks) | 7th | - | - | 14th (DNF) |
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| 8/2/2019 | Farmer City Raceway - Farmer City, IL 5th Annual What Up Dog 40 Street Stocks: Midwest Stock Car Tour A Modifieds, Dirt Late Models, Pro Late Model | Results | | Tommy Pickering (Street Stocks) | 6th | - | 8th | - |
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| 8/9/2019 | Farmer City Raceway - Farmer City, IL A Modifieds, Street Stocks, Dirt Late Models, Hornets, Pro Late Model | Results | | Tommy Pickering (Street Stocks) | 5th | - | - | 9th |
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| 8/16/2019 | Farmer City Raceway - Farmer City, IL A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Tommy Pickering (Street Stocks) | 5th | - | - | 10th |
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| 8/23/2019 | Farmer City Raceway - Farmer City, IL Dirt Super Late Models, A Modifieds, Street Stocks, Dirt Late Models, Hornets, Pro Late Model | Results | | Tommy Pickering (Street Stocks) | 5th | - | - | 5th |
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| 8/30/2019 | Farmer City Raceway - Farmer City, IL A Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Tommy Pickering (Street Stocks) | 3rd | - | - | 9th |
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| 9/7/2019 | Macon Speedway - Macon, IL Skeff Distributing Presents Taylorville Night with Spectator Drags / Hornet World Championship DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Tommy Pickering (Street Stocks) | 7th (DNF) | - | - | 14th (DNF) |
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| 9/14/2019 | Macon Speedway - Macon, IL Midgets: POWRi Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks | Results | | Tommy Pickering (Street Stocks) | 7th | - | - | 15th (DNF) |
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| 9/21/2019 | Macon Speedway - Macon, IL Midgets: POWRi National Midgets DIRTcar UMP Modifieds, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Tommy Pickering (Street Stocks) | 5th | - | - | 9th |
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| 9/28/2019 | Macon Speedway - Macon, IL 2019 Season Championships Racing for the Cup plus Fan Giveways DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets | Results | | Tommy Pickering (Street Stocks) | 3rd | - | - | 4th |
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