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| 1/3/2020 | Vado Speedway Park - Vado, NM Battle at the Border Dirt Super Late Models: World of Outlaws - Late Models USRA B-Mods, USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 1/4/2020 | Vado Speedway Park - Vado, NM Battle at the Border Dirt Super Late Models: World of Outlaws - Late Models USRA B-Mods, USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 2nd |
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| 1/5/2020 | Vado Speedway Park - Vado, NM Battle at the Border Dirt Super Late Models: World of Outlaws - Late Models USRA B-Mods, USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 1/10/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Practice A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds | No Results |
| 1/11/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, USRA B-Mods, USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 4th |
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| 1/12/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, USRA B-Mods, USRA Modifieds, IMCA Modified | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 1/14/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Practice A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, Supermodifieds, USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | - |
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| 1/15/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, USRA Modifieds, IMCA Modified | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 1/17/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 2nd |
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| 1/18/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 3rd |
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| 1/19/2020 | Arizona Speedway - Queen Creek, AZ Wild West Shootout A Modifieds: Wild West Shootout Dirt Super Late Models, B Modifieds, USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 1/30/2020 | Golden Isles Speedway - Waynesville, GA Super Bowl of Racing Practice Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | - |
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| 1/31/2020 | Golden Isles Speedway - Waynesville, GA Rhino Ag Super Bowl of Racing - Presented by General Tire Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Rain Out |
| 2/1/2020 | Golden Isles Speedway - Waynesville, GA RhinoAg Super Bowl 2020 Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 3rd |
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| 2/3/2020 | East Bay Raceway Park - Tampa, FL 44th Annual Wrisco Industries Winternationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 10th |
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| 2/4/2020 | East Bay Raceway Park - Tampa, FL 44th Annual Wrisco Industries Winternationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 2/5/2020 | East Bay Raceway Park - Tampa, FL 44th Annual Wrisco Industries Winternationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 3rd |
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| 2/6/2020 | East Bay Raceway Park - Tampa, FL 44th Annual Wrisco Industries Winternationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 1st |
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| 2/7/2020 | East Bay Raceway Park - Tampa, FL 44th Annual Wrisco Industries Winternationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 3rd |
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| 2/8/2020 | East Bay Raceway Park - Tampa, FL 44th Annual Wrisco Industries Winternationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 1st |
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| 2/9/2020 | All-Tech Raceway - Lake City, FL Winternationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series Street Stocks | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 3rd |
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| 2/10/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Brandon Sheppard (DIRTcar Late Models) | 1st | - | - | 1st |
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| 2/11/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar Late Models, Dirt Big Block Modifieds | Results | | Brandon Sheppard (DIRTcar Late Models) | 1st | - | - | 2nd |
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| 2/12/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 1st |
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| 2/13/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 6th |
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| 2/14/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 4th |
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| 2/15/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 5th |
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| 3/6/2020 | Duck River Raceway Park - Shelbyville, TN World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models Hobby Stocks, Street Stocks, Dirt Late Models, Pro Late Model, Pony Stock, Dirt Crate Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 4th |
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| 3/7/2020 | Smoky Mountain Speedway - Maryville, TN Tennessee Tipoff Dirt Super Late Models: World of Outlaws - Late Models Sportsmans, Dirt Crate Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 4th |
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| 5/9/2020 | Federated Auto Parts I-55 Raceway - Pevely, MO Federated Weekly Racing DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds | Results | | Brandon Sheppard (DIRTcar Late Models) | 2nd | - | - | 2nd |
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| 5/18/2020 | Golden Isles Speedway - Waynesville, GA Practice Golden Isles Speedway Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | - |
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| 5/19/2020 | Golden Isles Speedway - Waynesville, GA The OPTIMA Batteries Golden Isles Nationals Presented By Bilstein Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 14th |
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| 5/20/2020 | Golden Isles Speedway - Waynesville, GA The OPTIMA Batteries Golden Isles Nationals Presented By Bilstein Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 5th | - | 1st | 9th |
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| 5/21/2020 | Golden Isles Speedway - Waynesville, GA The OPTIMA Batteries Golden Isles Nationals Presented By Bilstein Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | DNS | - | DNS | - |
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| 5/22/2020 | Jackson Motorplex - Jackson, MN WORLD OF OUTLAWS - Late Models 360 Sprints - Winged: Midwest Sprint Touring Series with Midwest Power Series Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models: Tri-State Late Models 305 Sprints - Winged | Results | | Brandon Sheppard (Dirt Super Late Models) | 4th | - | - | 2nd |
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| 5/23/2020 | Jackson Motorplex - Jackson, MN WORLD OF OUTLAWS- Late Models Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models: Tri-State Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 3rd |
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| 5/29/2020 | Davenport Speedway - Davenport, IA Morton Buildings World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 5/30/2020 | Davenport Speedway - Davenport, IA Morton Buildings World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 6/4/2020 | Eldora Speedway - Rossburg, OH Dirt Late Model Stream Dirt Super Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 3rd |
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| 6/5/2020 | Eldora Speedway - Rossburg, OH Dirt Late Model Stream Dirt Super Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 6th |
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| 6/6/2020 | Eldora Speedway - Rossburg, OH Dirt Late Model Stream Dirt Super Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 4th |
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| 6/12/2020 | Cherokee Speedway - Gaffney, SC 22nd Annual Grassy Smith Memorial Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 2nd |
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| 6/13/2020 | Smoky Mountain Speedway - Maryville, TN Ole Smoky Moonshine Classic Dirt Super Late Models: Lucas Oil Late Model Dirt Series Sportsmans, Dirt Crate Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 6/19/2020 | Volunteer Speedway - Bulls Gap, TN World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 1st |
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| 6/20/2020 | Volunteer Speedway - Bulls Gap, TN World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models Dirt Crate Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 8th |
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| 6/25/2020 | Lernerville Speedway - Sarver, PA Firecracker Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 22nd |
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| 6/26/2020 | Lernerville Speedway - Sarver, PA Firecracker Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 6/27/2020 | Lernerville Speedway - Sarver, PA Firecracker 100 Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 6th |
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| 7/2/2020 | Cedar Lake Speedway - New Richmond, WI FVP Platinum Battery Showdown 410 Sprints - Winged: World of Outlaws 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Dirt Super Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 3rd |
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| 7/3/2020 | Cedar Lake Speedway - New Richmond, WI FVP Platinum Battery Showdown 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 2nd |
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| 7/4/2020 | Cedar Lake Speedway - New Richmond, WI 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 7/10/2020 | Outagamie Speedway - Seymour, WI World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models IMCA Modified, IMCA Stock Car | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 1st |
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| 7/11/2020 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 7/14/2020 | Gondik Law Speedway - Superior, WI World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models WISSOTA Midwest Mods, WISSOTA Hornet | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 7/18/2020 | Red River Valley Speedway - West Fargo, ND World of Outlaw Late Models Dirt Super Late Models: World of Outlaws - Late Models Sprint Cars, Stock Cars, B Modifieds, Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 7/19/2020 | River Cities Speedway - Grand Forks, ND Dirt Super Late Models: World of Outlaws - Late Models B Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 7/23/2020 | I-80 Speedway - Greenwood, NE Malvern Bank Go 50 Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 3rd |
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| 7/24/2020 | I-80 Speedway - Greenwood, NE 10th Annual Imperial Tile Silver Dollar Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds: USMTS - United States Modified Touring Series IMCA Modified | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | - |
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| 7/25/2020 | I-80 Speedway - Greenwood, NE 10th Annual Imperial Tile Silver Dollar Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds: USMTS - United States Modified Touring Series IMCA Modified | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 1st |
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| 7/28/2020 | Davenport Speedway - Davenport, IA World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models B Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 7/31/2020 | Kokomo Speedway - Kokomo, IN World Of Outlaws Morton Buildings Late Model Series Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | - |
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| 8/4/2020 | Beaver Dam Raceway - Beaver Dam, WI World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models Semi-Pro Legends | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 6th |
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| 8/6/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models USRA Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 9th |
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| 8/7/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds, Dirt Late Models, USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 5th | - | - | - |
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| 8/8/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models, USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 16th (DNF) |
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| 8/15/2020 | Federated Auto Parts I-55 Raceway - Pevely, MO UMP DIRTcar Summer Nationals DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds | Results | | Brandon Sheppard (DIRTcar Late Models) | 1st | - | - | 1st |
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| 8/27/2020 | Port Royal Speedway - Port Royal, PA Rumble by the River - Round 1 Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 8th |
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| 8/28/2020 | Port Royal Speedway - Port Royal, PA Dirt Track Throwback Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds | Rain Out |
| 8/29/2020 | Port Royal Speedway - Port Royal, PA Dirt Track Throwback Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 2nd |
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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 | | Brandon Sheppard (DIRTcar Late Models) | 2nd | - | - | 1st |
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| 9/17/2020 | I-80 Speedway - Greenwood, NE Al Belt Custom Homes I-80 Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series Stock Cars | Results | | Brandon Sheppard (Dirt Super Late Models) | 6th | - | 2nd | 12th |
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| 9/18/2020 | I-80 Speedway - Greenwood, NE Al Belt Custom Homes I-80 Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 4th | - | - | 10th |
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| 9/19/2020 | I-80 Speedway - Greenwood, NE Al Belt Custom Homes I-80 Nationals Dirt Super Late Models: SLMR Late Model Series with Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 6th |
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| 10/10/2020 | Fairbury Speedway - Fairbury, IL 10/10/2020 DIRTcar Late Models, DIRTcar UMP Modifieds, Pro Late Model | Results | | Brandon Sheppard (DIRTcar Late Models) | 1st | - | - | 1st |
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| 10/16/2020 | Portsmouth Raceway Park - Portsmouth, OH 40th Annual Dirt Track World Championship Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds: Renegades of Dirt Modified Tour Pro Legends, Economy Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | - |
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| 10/17/2020 | Portsmouth Raceway Park - Portsmouth, OH 40th Annual Dirt Track World Championship Dirt Super Late Models: Lucas Oil Late Model Dirt Series Economy Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 1st |
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| 10/30/2020 | Lakeside Speedway - Kansas City, KS 5th Annual Grant Junghans Memorial Dirt Super Late Models, USRA B-Mods, USRA Modifieds, IMCA Modified | Results | | Brandon Sheppard (USRA Modifieds) | 10th | - | 5th | - |
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| 10/31/2020 | 81 Speedway - Park City, KS Modified Spooktacular $10,031 to Win! Dirt Super Late Models, USRA B-Mods, USRA Modifieds, IMCA Modified | Results | | Brandon Sheppard (USRA Modifieds) | 2nd | - | - | 10th |
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| 11/1/2020 | Humboldt Speedway - Humboldt, KS USRA Halloween Hangover Dirt Super Late Models, Midwest Modifieds, B Modifieds, USRA B-Mods, USRA Modifieds, USRA Tuners, IMCA Modified | Results | | Brandon Sheppard (USRA Modifieds) | 8th | - | 1st | 6th |
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| 11/6/2020 | RPM Speedway - Crandall, TX USRA/USMTS Summit Southern Nationals A Modifieds: USMTS - United States Modified Touring Series Dirt Super Late Models, USRA B-Mods, USRA Limited Mods, USRA Modifieds, USRA Factory Stocks, USRA Tuners | Results | | Brandon Sheppard (A Modifieds) | 1st | - | - | 1st |
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| 11/7/2020 | RPM Speedway - Crandall, TX USRA/USMTS Summit Southern Nationals A Modifieds: USMTS - United States Modified Touring Series Dirt Super Late Models, USRA B-Mods, USRA Limited Mods, USRA Modifieds, USRA Factory Stocks, USRA Tuners | Results | | Brandon Sheppard (A Modifieds) | 1st | - | - | 1st |
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