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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 | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 8th |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 6th |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 1st |
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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 | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 25th |
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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 | | Cade Dillard (Dirt Super Late Models) | 11th | - | 4th | 22nd |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 18th |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 10th |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 4th |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 20th |
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| 2/10/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Cade Dillard (DIRTcar Late Models) | 5th | - | - | 11th |
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| 2/11/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar Late Models, Dirt Big Block Modifieds | Results | | Cade Dillard (DIRTcar Late Models) | 3rd | - | - | 15th |
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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 | | Cade Dillard (Dirt Super Late Models) | 4th | - | 1st | 17th |
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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 | | Cade Dillard (Dirt Super Late Models) | 4th | - | 3rd | 24th |
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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 | | Cade Dillard (Dirt Super Late Models) | 5th | - | 1st | 12th |
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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 | | Cade Dillard (Dirt Super Late Models) | 5th | - | 1st | 20th |
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| 2/28/2020 | I-37 Speedway - Pleasanton, TX USMTS A Modifieds: USMTS - United States Modified Touring Series USRA Limited Mods, USRA Factory Stocks | Results | | Cade Dillard (A Modifieds) | 4th | - | 1st | 24th |
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| 2/29/2020 | South Texas Race Ranch - Corpus Christi, TX 4th Annual USMTS Sparkling City Nationals A Modifieds: USMTS - United States Modified Touring Series USRA Limited Mods, USRA Factory Stocks | Results | | Cade Dillard (A Modifieds) | 4th | - | 1st | 6th |
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| 3/1/2020 | Cotton Bowl Speedway - Paige, TX 2nd Annual USMTS Event A Modifieds: USMTS - United States Modified Touring Series USRA Limited Mods, USRA Factory Stocks | Results | | Cade Dillard (A Modifieds) | 2nd | - | - | 23rd |
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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 | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 5th |
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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 | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 21st |
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| 5/1/2020 | RPM Speedway - Crandall, TX Round #1 KR Promotions Cup Limited Sport Mod, USRA Limited Mods, USRA Modifieds, USRA Factory Stocks, USRA Tuners | Results | | Cade Dillard (USRA Modifieds) | 1st | - | - | 3rd |
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| 5/15/2020 | Magnolia Motor Speedway - Columbus, MS Magnolia Mayhem 40 Dirt Super Late Models | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 13th |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 12th |
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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 | | Cade Dillard (Dirt Super Late Models) | 4th | - | - | 8th |
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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 | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 13th |
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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 | | Cade Dillard (Dirt Super Late Models) | 5th | - | 2nd | 4th |
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| 6/11/2020 | Cedar Lake Speedway - New Richmond, WI MASTERS Day 1 A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Modifieds, USRA Late Models, IMCA Modified | Results | | Cade Dillard (A Modifieds) | 7th | - | 11th | - | | Cade Dillard (Dirt Late Models) | 1st | - | - | 12th |
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| 6/12/2020 | Cedar Lake Speedway - New Richmond, WI MASTERS Day 2 A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Modifieds, USRA Late Models, IMCA Modified | Results | | Cade Dillard (A Modifieds) | 3rd | - | 5th | - | | Cade Dillard (Dirt Late Models) | 2nd | - | - | 6th |
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| 6/13/2020 | Cedar Lake Speedway - New Richmond, WI Masters Day 3 A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA Modifieds, USRA Late Models, IMCA Modified | Results | | Cade Dillard (A Modifieds) | 1st | - | - | 4th | | Cade Dillard (Dirt Late Models) | 3rd | - | - | 3rd |
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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 | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 3rd |
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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 | | Cade Dillard (Dirt Super Late Models) | 7th (DNF) | - | DNS | 19th |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 2nd |
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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 | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 4th |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 1st |
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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 | | Cade Dillard (Dirt Super Late Models) | - | - | - | 1st |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 9th |
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| 7/4/2020 | Cedar Lake Speedway - New Richmond, WI 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 2nd |
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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 | | Cade Dillard (Dirt Super Late Models) | 4th | - | - | 7th |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 12th |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 2nd |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 6th |
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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 | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 2nd |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 2nd |
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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 | | Cade Dillard (Dirt Super Late Models) | - | - | - | 3rd |
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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 | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 3rd |
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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 | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 6th |
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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 | | Cade Dillard (Dirt Super Late Models) | 4th | - | - | - |
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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 | | Cade Dillard (Dirt Super Late Models) | - | - | - | 11th |
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| 8/20/2020 | Lincoln Speedway - Abbottstown, PA | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 4th |
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| 8/21/2020 | Williams Grove Speedway - Mechanicsburg, PA World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models 410 Sprints - Winged | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 12th |
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| 8/22/2020 | Eriez Speedway - Erie, PA World of Outlaws Super Late Models, Vogt Memorial Econo-Mod Race $1000 to win Dirt Super Late Models, B Modifieds, Sport Compact | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 6th |
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| 9/4/2020 | Lavonia Speedway - Lavonia, GA | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 9th |
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| 9/5/2020 | Lancaster Motor Speedway - Lancaster, SC World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 19th |
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| 9/11/2020 | Ark-La-Tex Speedway - Vivian, LA A Modifieds: USMTS - United States Modified Touring Series Dirt Super Late Models, Pure Stock, USRA B-Mods, USRA Limited Mods, USRA Modifieds, USRA Factory Stocks, USRA Tuners | Results | | Cade Dillard (A Modifieds) | 2nd | - | - | 4th |
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| 9/12/2020 | Boothill Speedway - Greenwood, LA A Modifieds: USMTS - United States Modified Touring Series Dirt Super Late Models, Factory Stocks, CRUSA Dirt Late Models, Limited Modified, Sport Compact, USRA B-Mods, USRA Modifieds | Results | | Cade Dillard (A Modifieds) | 2nd | - | - | 18th |
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| 9/18/2020 | Revolution Park - Monroe, LA Dirt Super Late Models: MSCCS | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 1st |
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| 9/19/2020 | Revolution Park - Monroe, LA Dirt Super Late Models: MSCCS Dirt Crate Late Models | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 1st | | Cade Dillard (Dirt Crate Late Models) | - | - | - | 2nd |
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| 9/25/2020 | Thunder Mountain Speedway - Brookville, PA | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 13th |
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| 9/26/2020 | Thunder Mountain Speedway - Brookville, PA World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 12th |
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| 10/2/2020 | Cherokee Speedway - Gaffney, SC World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 12th |
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| 10/3/2020 | 411 Motor Speedway - Seymour, TN World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models Sportsmans, A Modifieds, Street Stocks, Vintage Modifieds, Dirt Crate Late Models | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 10th |
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| 10/17/2020 | Super Bee Speedway - Chatham, LA 360 Sprints - Winged: USCS United Sprint Car Series Dirt Super Late Models, Winged A-Class | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 1st |
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| 10/24/2020 | Whynot Motorsports Park - Meridian, MS Dirt Super Late Models, Dirt Late Models | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 2nd | | Cade Dillard (Dirt Late Models) | - | - | - | 5th |
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| 10/29/2020 | Tri-State Speedway - Pocola, OK CANCELLED - Modster Mash-Episode 1-King of the Ring USRA B-Mods, USRA Modifieds | Rain Out |
| 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 | | Cade Dillard (A Modifieds) | - | - | - | - | | Cade Dillard (USRA Modifieds) | 5th | - | 2nd | 6th |
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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 | | Cade Dillard (USRA Modifieds) | 4th | - | 1st | 13th |
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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 | | Cade Dillard (USRA Modifieds) | 4th | - | 2nd | 8th |
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| 11/4/2020 | The Dirt Track at Charlotte - Concord, NC | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 8th |
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| 11/5/2020 | The Dirt Track at Charlotte - Concord, NC Can-Am World Finals Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 12th |
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| 11/13/2020 | Magnolia Motor Speedway - Columbus, MS | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 13th |
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| 11/14/2020 | Magnolia Motor Speedway - Columbus, MS Dirt Super Late Models, Dirt Crate Late Models | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 17th |
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