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| 1/31/2020 | Tri City Speedway - Granite City, IL Clash at the Coliseum Weekend 3 Winged Outlaw, Junior 2 Animal Dirt Karts, Flat RWYB, 500 Winged Open Outlaw, Clone Heavy Dirt Karts, Clone Medium Dirt Karts, Clone Super Heavy Dirt Karts, LO 206 Cage Adult Winged, LO 206 Cage Junior 1 Winged, Flat Jr. 1 Clone, Predator Maxxis, Predator Hoosier | Results | | Tommy Sheppard Jr (Flat RWYB) | - | - | - | 5th |
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| 2/29/2020 | Clarksville Speedway - Clarksville, TN Tuckasee Toilet Bowl DIRTcar Late Models, DIRTcar UMP Modifieds, Street Stocks, Dwarf, Hornets, Economy Late Models, 600cc Modifieds, Dirt Crate Late Models, Mod Lites | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 2nd | - | - | 3rd |
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| 5/9/2020 | I-55 Federated Auto Parts Raceway Park - Pevely, MO Federated Weekly Racing DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 4th | - | - | 20th |
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| 6/6/2020 | Charleston Speedway - Charleston, IL DIRTcar UMP Modifieds, B Modifieds, Street Stocks, Hornets, Economy Late Models | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 3rd | - | 1st | 18th |
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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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | DNS | - | - | 7th |
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| 6/24/2020 | Fairbury Speedway - Fairbury, IL June 24th 2020 DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 6th | - | 2nd | 10th |
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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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 4th | - | - | 6th |
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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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 3rd | - | - | 20th (DNF) |
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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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 1st | - | - | 5th | | Tommy Sheppard Jr (Pro Late Model) | 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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 6th (DNF) | - | - | 4th | | Tommy Sheppard Jr (Pro Late Model) | 4th | - | - | - |
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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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 7th (DNF) | - | - | 5th |
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| 7/18/2020 | Fairbury Speedway - Fairbury, IL July 18, 2020 DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 6th | - | 1st | 7th |
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| 7/24/2020 | Farmer City Raceway - Farmer City, IL 10th Annual Jr. Kimler Memorial $3K Late Models + Full Show DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 5th | - | - | 7th |
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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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 2nd | - | - | 2nd |
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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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 2nd | - | - | 3rd |
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| 8/8/2020 | Macon Speedway - Macon, IL Regular Night of Racing at Mighty Macon Speedway DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 1st | - | - | 1st |
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| 8/13/2020 | Macon Speedway - Macon, IL Herald & Review 100 Summernationals DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 1st | - | - | 22nd (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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 3rd | - | - | 16th (DNF) |
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| 8/16/2020 | Lincoln Speedway - Lincoln, IL Graue Chevrolet Summernationals featuring the HELL TOUR 305 Sprints - Winged, Dirt Super Late Models, DIRTcar UMP Modifieds | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 6th | - | 2nd | 11th |
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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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 2nd | - | - | 10th |
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| 8/22/2020 | Macon Speedway - Macon, IL Camfield Memorial Midgets: POWRi DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks, Hornets | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 1st | - | - | 1st |
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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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 6th | - | - | 8th |
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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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 4th | - | - | 4th |
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| 9/5/2020 | Macon Speedway - Macon, IL Regular Night of Weekly Racing DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 2nd | - | - | 1st |
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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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 1st | - | - | 1st |
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| 9/15/2020 | Fairbury Speedway - Fairbury, IL "One for the Road" Late Model Special DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 6th | - | 8th (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 | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 1st | - | - | 1st |
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| 9/26/2020 | Macon Speedway - Macon, IL Season Championship "Racing for Cup" and Give Back to the fans DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Tommy Sheppard Jr (DIRTcar UMP Modifieds) | 2nd | - | - | 1st |
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