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| 1/13/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Sunshine Nationals - Practice Night Dirt Super Late Models: World of Outlaws - Late Models CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Late Models, Dirt Crate Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | - |
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| 1/14/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Sunshine Nationals - Night #1 Dirt Super Late Models: World of Outlaws - Late Models CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Late Models, Dirt Crate Late Models | Results | | Chris Madden (Dirt Super Late Models) | 4th | - | - | 13th |
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| 1/15/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Sunshine Nationals - Night #2 Dirt Super Late Models: World of Outlaws - Late Models CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Late Models, Dirt Crate Late Models | Rain Out |
| 1/16/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Sunshine Nationals - Night #3 Dirt Super Late Models: World of Outlaws - Late Models CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Late Models, Dirt Crate Late Models | Results | | Chris Madden (Dirt Super Late Models) | 7th | - | 4th | - |
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| 2/8/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #7 (DIRTcar UMP Modifieds Gator Championship Night 4) DIRTcar UMP Modifieds, DIRTcar Pro Late Models | Results | | Chris Madden (DIRTcar Pro Late Models) | 5th | - | 4th | - |
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| 2/9/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #8 DIRTcar Big Block Modifieds: Super DIRTCar Series DIRTcar Pro Late Models | Results | | Chris Madden (DIRTcar Pro Late Models) | 3rd | - | - | 13th |
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| 2/10/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #9 Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Chris Madden (Dirt Super Late Models) | 7th | - | 5th | - |
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| 2/11/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #10 Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Chris Madden (Dirt Super Late Models) | 1st | - | - | 8th |
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| 2/12/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #11 Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Chris Madden (Dirt Super Late Models) | 2nd | - | - | 4th |
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| 2/27/2021 | Modoc Raceway - Modoc, SC Drydene Xtreme DIRTcar Series DIRTcar Late Models | Results | | Chris Madden (DIRTcar Late Models) | - | - | - | 6th |
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| 3/6/2021 | Smoky Mountain Speedway - Maryville, TN 8th Annual Tennessee Tipoff Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models, Hornets | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 1st |
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| 3/19/2021 | Bristol Motor Speedway - Bristol, TN Bristol Dirt Nationals Dirt Super Late Models: XR Workin' Man Series DIRTcar UMP Modifieds | Results | | Chris Madden (Dirt Super Late Models) | 2nd | - | - | 5th |
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| 3/20/2021 | Bristol Motor Speedway - Bristol, TN Bristol Dirt Nationals Dirt Super Late Models: XR Workin' Man Series DIRTcar UMP Modifieds, Stock Cars, A Modifieds, Hornets, IMCA Sport Compact, 604 Crate Late Models | Results | | Chris Madden (Dirt Super Late Models) | 3rd | - | - | 8th |
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| 3/26/2021 | Cherokee Speedway - Gaffney, SC ROCK GAULT MEMORIAL Dirt Super Late Models: World of Outlaws - Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | - |
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| 4/2/2021 | Farmer City Raceway - Farmer City, IL Triple Qualifying Features $600 to win $100 to start Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: Summit American Modified Series Street Stocks, Dirt Late Models, Pro Late Model | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 18th |
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| 4/3/2021 | Farmer City Raceway - Farmer City, IL $2500 to win $150 to start Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: Summit American Modified Series Dirt Late Models, Pro Late Model | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 4th |
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| 5/7/2021 | Mississippi Thunder Speedway - Fountain City, WI Dairyland Showdown with World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, USRA Modifieds | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 5th |
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| 5/8/2021 | Mississippi Thunder Speedway - Fountain City, WI Dairyland Showdown with World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, USRA Modifieds | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 1st |
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| 5/21/2021 | Port Royal Speedway - Port Royal, PA HUEY WILCOXON MEMORIAL Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 1st |
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| 5/22/2021 | Port Royal Speedway - Port Royal, PA Dirt Super Late Models: World of Outlaws - Late Models 410 Sprints - Winged, Dirt Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 1st |
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| 6/24/2021 | Lernerville Speedway - Sarver, PA "Bill Emig Memorial" - Night 1 Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series Dirt Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 2nd |
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| 6/25/2021 | Lernerville Speedway - Sarver, PA "Bill Emig Memorial" - Night 2 Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series Dirt Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 9th |
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| 6/26/2021 | Lernerville Speedway - Sarver, PA "Bill Emig Memorial" - Night 3 Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series Dirt Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 2nd |
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| 7/9/2021 | Jackson Motorplex - Jackson, MN World of Outlaws Morton Buildings Late Model Series Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models: Tri-State Late Models | Results | | Chris Madden (Dirt Super Late Models) | 6th | - | - | 4th |
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| 7/10/2021 | Jackson Motorplex - Jackson, MN World of Outlaws Morton Buildings Late Model Series Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models: Tri-State Late Models | Results | | Chris Madden (Dirt Super Late Models) | 4th | - | - | 4th |
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| 7/13/2021 | Gondik Law Speedway - Superior, WI World of Outlaws Late Model Special Dirt Super Late Models: World of Outlaws - Late Models WISSOTA Modifieds, WISSOTA Hornet | Results | | Chris Madden (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 7/18/2021 | Red Cedar Speedway - Menomonie, WI World of Outlaws Late Models & $1,000 to Win Open Modifieds w/ Limited Late Models Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, Dirt Limited Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 3rd |
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| 7/31/2021 | Fairbury Speedway - Fairbury, IL PRAIRIE DIRT CLASSIC Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: DIRTcar Modified Nationals DIRTcar Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 4th |
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| 8/3/2021 | Outagamie Speedway - Seymour, WI FVP Platinum Batteries Showdown featuring the Morton Buildings World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models IMCA Modified, IMCA Stock Car | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 3rd |
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| 8/5/2021 | Cedar Lake Speedway - New Richmond, WI 34th Annual USA Nationals Night 1 Dirt Super Late Models: World of Outlaws - Late Models USRA Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 10th |
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| 8/6/2021 | Cedar Lake Speedway - New Richmond, WI 34th Annual USA Nationals Night 2 Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Chris Madden (Dirt Super Late Models) | 5th | - | - | - |
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| 8/7/2021 | Cedar Lake Speedway - New Richmond, WI 34th Annual USA Nationals Night 3 Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 14th |
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| 8/26/2021 | Davenport Speedway - Davenport, IA Quad Cities 150 presented by Hoker Trucking Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, B Modifieds, IMCA Modified | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 10th |
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| 8/27/2021 | Davenport Speedway - Davenport, IA Quad Cities 150 presented by Hoker Trucking Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, B Modifieds, IMCA Modified | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 5th |
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| 8/28/2021 | Davenport Speedway - Davenport, IA Quad Cities 150 presented by Hoker Trucking Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, B Modifieds, IMCA Modified | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 6th |
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| 9/2/2021 | Cherokee Speedway - Gaffney, SC ROCK GAULT MEMORIAL Dirt Super Late Models: World of Outlaws - Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 2nd |
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| 9/3/2021 | Lavonia Speedway - Lavonia, GA World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 10th |
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| 9/17/2021 | Texas Motor Speedway - Fort Worth, TX Dirt Super Late Models: XR Workin' Man Series USRA Modifieds | Results | | Chris Madden (Dirt Super Late Models) | 1st | - | - | 16th (DNF) |
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| 9/18/2021 | Texas Motor Speedway - Fort Worth, TX Dirt Super Late Models: XR Workin' Man Series USRA Modifieds | Results | | Chris Madden (Dirt Super Late Models) | 3rd | - | - | 23rd (DNF) |
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| 10/1/2021 | Cherokee Speedway - Gaffney, SC MIKE DUVALL MEMORIAL Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Chris Madden (Dirt Super Late Models) | - | - | - | 5th |
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| 10/9/2021 | Dixie Speedway - Woodstock, GA Lucas Oil Dixie Shootout Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Chris Madden (Dirt Super Late Models) | 1st | - | - | 3rd |
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| 10/10/2021 | Rome Speedway - Rome, GA Lucas Oil Rome Showdown Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models, CRUSA Modified Sportsman | Results | | Chris Madden (Dirt Super Late Models) | 2nd | - | - | 19th |
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| 11/4/2021 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Postponed |
| 11/5/2021 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Chris Madden (Dirt Super Late Models) | 3rd | - | - | 10th |
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| 11/6/2021 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Chris Madden (Dirt Super Late Models) | 1st | - | - | 5th |
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| 11/12/2021 | Senoia Raceway - Senoia, GA Peach State Classic Dirt Super Late Models, Hobby Stocks, Sportsmans | Results | | Chris Madden (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 11/13/2021 | Senoia Raceway - Senoia, GA Peach State Classic Dirt Super Late Models, Dirt Crate Late Models, Asphalt Bombers | Results | | Chris Madden (Dirt Super Late Models) | 1st | - | - | 1st |
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| 11/21/2021 | Cherokee Speedway - Gaffney, SC 31st Annual Blue Gray 100 DIRTcar Late Models: Xtreme DIRTcar Series | Results | | Chris Madden (DIRTcar Late Models) | 1st | - | - | 1st |
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