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| 1/29/2021 | Screven Motor Speedway - Sylvania, GA $8,000 to win 410 Sprints - Winged: All Star Circuit of Champions A Modifieds: Southeastern Modified Series | Results | | Kerry Madsen (410 Sprints - Winged) | 3rd | - | - | 12th |
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| 1/30/2021 | Screven Motor Speedway - Sylvania, GA $10,000 to win 410 Sprints - Winged: All Star Circuit of Champions A Modifieds: Southeastern Modified Series | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | 5th | - | 7th |
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| 2/2/2021 | East Bay Raceway Park - Tampa, FL $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 3rd |
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| 2/3/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 11th |
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| 2/4/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | - | - | 13th |
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| 2/5/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #4 (DIRTcar UMP Modifieds Gator Championship Night 1) 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Kerry Madsen (410 Sprints - Winged) | DNS | - | DNS | - |
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| 2/7/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #6 (DIRTcar UMP Modifieds Gator Championship Night 3) 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | - | - | 7th |
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| 3/6/2021 | Lincoln Speedway - Abbottstown, PA | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 11th |
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| 3/13/2021 | Port Royal Speedway - Port Royal, PA 410 Sprints - Winged, Dirt Super Late Models | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | - | - | 2nd |
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| 3/14/2021 | Williams Grove Speedway - Mechanicsburg, PA | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 17th |
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| 3/20/2021 | Port Royal Speedway - Port Royal, PA 410 Sprints - Winged, Dirt Super Late Models | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 15th |
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| 3/26/2021 | Williams Grove Speedway - Mechanicsburg, PA | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | - | - | 10th |
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| 3/27/2021 | Port Royal Speedway - Port Royal, PA 410 Sprints - Winged, Dirt Super Late Models | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 8th |
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| 3/27/2021 | Selinsgrove Raceway Park - Sellinsgrove, PA | Results | | Kerry Madsen (410 Sprints - Winged) | - | - | - | - |
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| 4/3/2021 | Port Royal Speedway - Port Royal, PA National Open 410 Sprints - Winged, Dirt Super Late Models | Results | | Kerry Madsen (410 Sprints - Winged) | 3rd | - | - | 10th |
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| 4/6/2021 | Bridgeport Motorsports Park - Bridgeport, NJ | Results | | Kerry Madsen (410 Sprints - Winged) | 3rd | 2nd | - | 1st |
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| 4/10/2021 | Port Royal Speedway - Port Royal, PA National Open 360 Sprints - Non-Winged: USAC East Coast Sprint Cars 410 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | - | - | 10th |
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| 4/15/2021 | Virginia Motor Speedway - Jamaica, VA $12,000 to win 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | - | - | 2nd |
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| 4/16/2021 | Williams Grove Speedway - Mechanicsburg, PA The Tommy Hinnershitz Classic -$6,000 to win 410 Sprints - Winged: All Star Circuit of Champions 358 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 4th | - | 8th |
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| 4/17/2021 | Port Royal Speedway - Port Royal, PA Keith Kauffman Classic $10,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 4th | - | 26th (DNF) |
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| 4/18/2021 | Bedford Speedway - Bedford, PA Johnny Grum Classic $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | - | - | 13th |
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| 4/23/2021 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged, 358 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 7th | - | 2nd | 11th |
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| 4/24/2021 | Lincoln Speedway - Abbottstown, PA | Results | | Kerry Madsen (410 Sprints - Winged) | 6th | - | - | 24th (DNF) |
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| 4/25/2021 | Selinsgrove Raceway Park - Sellinsgrove, PA | Results | | Kerry Madsen (410 Sprints - Winged) | 3rd | - | - | 7th |
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| 4/25/2021 | Selinsgrove Speedway - Selinsgrove, PA Ray Tilley Classic 410 Sprints - Winged, Dirt Super Late Models | Results | | Kerry Madsen (410 Sprints - Winged) | 3rd | - | - | 7th |
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| 4/30/2021 | Lernerville Speedway - Sarver, PA Lernerville Grand $7,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Rain Out |
| 5/1/2021 | Port Royal Speedway - Port Royal, PA 410 Sprints - Winged, Dirt Super Late Models | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 14th |
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| 5/1/2021 | Sharon Speedway - Hartford, OH Buckeye Cup $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | - | - | - | - |
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| 5/2/2021 | BAPS Motor Speedway - York Haven, PA Select Collision Kevin Gobrecht Classic ($5 off GA to ALL Fans Wearing a Kevin Gobrecht T-Shirt) 410 Sprints - Winged, Supermodifieds | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 6th |
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| 5/2/2021 | Tri City Raceway Park - Franklin, PA $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | - | - | - | - |
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| 5/7/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged: USAC National Sprint Cars | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | - | - | 7th |
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| 5/8/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged: USAC National Sprint Cars | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 13th |
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| 5/14/2021 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | 7th | - | 6th |
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| 5/15/2021 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | 3rd | - | 5th |
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| 5/20/2021 | Circle City Raceway - Indianapolis, IN All Star Indiana Invasion presented by Rayce Rudeen Foundation $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions TQ Midgets: All Star TQ Midgets | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | 3rd | - | 8th |
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| 5/21/2021 | Circle City Raceway - Indianapolis, IN All Star Indiana Invasion presented by Rayce Rudeen Foundation $10,000 to win 410 Sprints - Winged: All Star Circuit of Champions 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 7th | - | 13th |
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| 5/22/2021 | Gas City I-69 Speedway - Gas City, IN All Star Indiana Invasion presented by Rayce Rudeen Foundation $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 5th (DNF) | - | 4th |
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| 5/23/2021 | Kokomo Speedway - Kokomo, IN All Star Indiana Invasion presented by Rayce Rudeen Foundation $26,000 to win 410 Sprints - Winged: All Star Circuit of Champions 410 Sprints - Non-Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 2nd | - | 18th (DNF) |
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| 5/28/2021 | Williams Grove Speedway - Mechanicsburg, PA Davey Brown Tribute Race - $10,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Rain Out |
| 5/29/2021 | Port Royal Speedway - Port Royal, PA Bob Weikert Memorial $10,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Rain Out |
| 5/30/2021 | Port Royal Speedway - Port Royal, PA Bob Weikert Memorial $29,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Rain Out |
| 5/31/2021 | Lawrenceburg Speedway - Lawrenceburg, IN 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 5th |
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| 6/5/2021 | Knoxville Raceway - Knoxville, IA McKay Group Night 360 Sprints - Winged, 410 Sprints - Winged, 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | - | - | 2nd |
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| 6/11/2021 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged, 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 1st | - | 3rd |
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| 6/12/2021 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | 2nd | - | 2nd |
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| 6/17/2021 | 34 Raceway - West Burlington, IA 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 5th | - | 4th |
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| 6/18/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA 410 Sprints - Winged: World of Outlaws A Modifieds | Results | | Kerry Madsen (410 Sprints - Winged) | 3rd | - | - | 3rd |
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| 6/19/2021 | Knoxville Raceway - Knoxville, IA 360 Sprints - Winged, 410 Sprints - Winged, 305 Sprints - Winged | Results | | Kerry Madsen (410 Sprints - Winged) | 3rd | - | - | 1st |
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| 6/21/2021 | Huset's Speedway - Brandon, SD The SHOWDOWN -HUSET'S 50 presented by BillionAuto.com 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 5th | - | 3rd |
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| 6/22/2021 | Huset's Speedway - Brandon, SD THE SHOWDOWN - HUSET'S 50 - presented by BillionAuto.com 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 3rd | - | - | 8th |
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| 6/24/2021 | Jackson Motorplex - Jackson, MN AGCO Jackson Nationals - THE SHOWDOWN 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 7th | - | - | 1st |
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| 6/25/2021 | Jackson Motorplex - Jackson, MN AGCO Jackson Nationals - THE SHOWDOWN 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 6th | - | 1st |
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| 6/26/2021 | Jackson Motorplex - Jackson, MN AGCO Jackson Nationals - THE SHOWDOWN 410 Sprints - Winged: World of Outlaws | Postponed |
| 6/27/2021 | Jackson Motorplex - Jackson, MN 43rd Annual AGCO Jackson Nationals 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | - | 2nd | - | 4th |
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| 7/14/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 4th | - | 4th |
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| 7/15/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | - | - | 22nd (DNF) |
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| 7/17/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 9th (DNF) | - | - | - |
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| 7/27/2021 | I-70 Speedway - Odessa, MO $7,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | 8th | - | 5th |
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| 7/29/2021 | Missouri State Fair Speedway - Sedalia, MO All Star Circuit of Champions 410 Sprints - Winged: All Star Circuit of Champions Non-Winged Sprints: POWRi WAR Sprints Midgets | Results | | Kerry Madsen (410 Sprints - Winged) | 4th | 4th | - | 2nd |
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| 7/30/2021 | 34 Raceway - West Burlington, IA American Hemp Research presents FloRacing All Star Circuit of Champions 410 Sprints - Winged: All Star Circuit of Champions 305 Sprints - Winged, Dirt Super Late Models | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | - | - | 1st |
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| 7/31/2021 | Knoxville Raceway - Knoxville, IA $7,000 to win 410 Sprints - Winged: All Star Circuit of Champions 360 Sprints - Winged, Winged Sprints | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 2nd | - | 1st |
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| 8/8/2021 | Knoxville Raceway - Knoxville, IA 10th annual Capitani Classic presented by Great Southern Bank 410 Sprints - Winged, Winged Sprints | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | - | - | 4th |
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| 8/12/2021 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged, Winged Sprints | Results | | Kerry Madsen (410 Sprints - Winged) | 7th | - | 2nd | 22nd |
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| 8/14/2021 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged, Winged Sprints | Results | | Kerry Madsen (410 Sprints - Winged) | - | - | 2nd | 11th |
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| 10/8/2021 | Port Royal Speedway - Port Royal, PA 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 2nd | 2nd | - | 1st |
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| 10/9/2021 | Port Royal Speedway - Port Royal, PA 410 Sprints - Winged: World of Outlaws | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 6th | - | 4th |
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| 10/22/2021 | Lakeside Speedway - Kansas City, KS 410 Sprints - Winged: World of Outlaws Mod Lites | Results | | Kerry Madsen (410 Sprints - Winged) | 1st | 2nd | - | 3rd |
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| 10/29/2021 | Lawton Speedway - Lawton, OK 410 Sprints - Winged: World of Outlaws USRA Limited Mods | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 10th |
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| 10/30/2021 | Devil's Bowl Speedway - Mesquite, TX World of Outlaws Texas Nationals 410 Sprints - Winged: World of Outlaws USRA Limited Mods | Results | | Kerry Madsen (410 Sprints - Winged) | 5th | - | - | 12th |
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| 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 | | Kerry Madsen (410 Sprints - Winged) | 1st | 5th | - | 2nd |
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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 | | Kerry Madsen (410 Sprints - Winged) | 4th | - | - | 6th |
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