| | Heat | Dash | B Feature | A Feature |
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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 | | Ian Madsen (410 Sprints - Winged) | 2nd | - | - | 10th |
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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 | | Ian Madsen (410 Sprints - Winged) | 8th (DNF) | - | DNS | - |
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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 | | Ian Madsen (410 Sprints - Winged) | 3rd | 1st | - | 2nd |
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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 | | Ian Madsen (410 Sprints - Winged) | 2nd | - | - | 19th |
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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 | | Ian Madsen (410 Sprints - Winged) | 2nd | - | - | 19th |
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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 | | Ian Madsen (410 Sprints - Winged) | 8th (DNF) | - | DNS | - |
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| 3/12/2021 | Magnolia Motor Speedway - Columbus, MS 410 Sprints - Winged: World of Outlaws CRUSA Late Model Sportsman | Results | | Ian Madsen (410 Sprints - Winged) | 5th | - | - | 10th |
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| 3/13/2021 | Revolution Park - Monroe, LA 410 Sprints - Winged: World of Outlaws | Results | | Ian Madsen (410 Sprints - Winged) | 3rd | - | - | 8th |
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| 3/19/2021 | Cotton Bowl Speedway - Paige, TX 410 Sprints - Winged: World of Outlaws Factory Stocks | Results | | Ian Madsen (410 Sprints - Winged) | 2nd | 3rd | - | 4th |
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| 3/20/2021 | Cotton Bowl Speedway - Paige, TX 410 Sprints - Winged: World of Outlaws IMCA Southern SportMod | Results | | Ian Madsen (410 Sprints - Winged) | 6th | - | - | 13th |
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| 3/27/2021 | Lake Ozark Speedway - Eldon, MO 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Ian Madsen (410 Sprints - Winged) | 5th | - | - | 13th |
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| 4/3/2021 | Attica Raceway Park - Attica, OH Core and Main Spring Nationals $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Ian Madsen (410 Sprints - Winged) | 3rd | 4th | - | 8th |
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| 4/9/2021 | Kokomo Speedway - Kokomo, IN 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged | Results | | Ian Madsen (410 Sprints - Winged) | 1st | 8th | - | 4th |
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| 4/10/2021 | Tri-State Speedway - Haubstadt, IN 410 Sprints - Winged: World of Outlaws | Results | | Ian Madsen (410 Sprints - Winged) | 1st | 4th | - | 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 | | Ian Madsen (410 Sprints - Winged) | 3rd | 2nd | - | 17th (DNF) |
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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 | | Ian Madsen (410 Sprints - Winged) | 1st | 2nd | - | 4th |
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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 | | Ian Madsen (410 Sprints - Winged) | 3rd | 3rd | - | 3rd |
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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 | | Ian Madsen (410 Sprints - Winged) | 3rd | 7th | - | 8th |
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| 4/24/2021 | Knoxville Raceway - Knoxville, IA 360 Sprints - Winged, 410 Sprints - Winged, 305 Sprints - Winged | Results | | Ian Madsen (410 Sprints - Winged) | 2nd | - | - | 2nd |
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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 | | Ian Madsen (410 Sprints - Winged) | 2nd | 2nd | - | 3rd |
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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 | | Ian Madsen (410 Sprints - Winged) | 4th | 1st | - | 3rd |
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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 | | Ian Madsen (410 Sprints - Winged) | 3rd | - | - | 6th |
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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 | | Ian Madsen (410 Sprints - Winged) | 1st | 1st | - | 4th |
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| 5/14/2021 | I-96 Speedway - Lake Odessa, MI Mace Thomas Classic - $8,500 to win 410 Sprints - Winged: All Star Circuit of Champions DIRTcar Late Models, Street Stocks | Results | | Ian Madsen (410 Sprints - Winged) | 4th | 1st | - | 2nd |
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| 5/15/2021 | Dirt Oval at Route 66 - Joliet, IL $8,000 to win 410 Sprints - Winged: IRA Interstate Racing Association with All Star Circuit of Champions Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Ian Madsen (410 Sprints - Winged) | 3rd | - | - | 7th |
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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 | | Ian Madsen (410 Sprints - Winged) | 2nd | 5th | - | 10th |
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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 | | Ian Madsen (410 Sprints - Winged) | 3rd | - | - | 16th |
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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 | | Ian Madsen (410 Sprints - Winged) | 6th | - | 2nd | 17th |
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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 | | Ian Madsen (410 Sprints - Winged) | 1st | 6th | - | 24th (DNF) |
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| 5/31/2021 | Port Royal Speedway - Port Royal, PA Bob Weikert Memorial $29,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Ian Madsen (410 Sprints - Winged) | 2nd | - | - | 10th |
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| 6/3/2021 | Fairbury Speedway - Fairbury, IL $5,000 to win 410 Sprints - Winged: IRA Interstate Racing Association with All Star Circuit of Champions DIRTcar Late Models | Results | | Ian Madsen (410 Sprints - Winged) | 1st | 4th | - | 4th |
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| 6/4/2021 | Wilmot Raceway - Wilmot, WI $6,000 to win 410 Sprints - Winged: IRA Interstate Racing Association with All Star Circuit of Champions Lightning Sprints: IRA Lightning Sprints Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Ian Madsen (410 Sprints - Winged) | 4th | 1st | - | 2nd |
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| 6/5/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI $6,000 to win 410 Sprints - Winged: IRA Interstate Racing Association with All Star Circuit of Champions 360 Sprints - Winged | Results | | Ian Madsen (410 Sprints - Winged) | 2nd | 1st | - | 2nd |
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| 6/6/2021 | Angell Park Speedway - Sun Prairie, WI $6,000 to win 410 Sprints - Winged: IRA Interstate Racing Association with All Star Circuit of Champions Badger Midgets: Badger Midget Auto Racing Association | Results | | Ian Madsen (410 Sprints - Winged) | 4th | 5th | - | 2nd |
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| 6/11/2021 | Attica Raceway Park - Attica, OH Ohio Sprint Speedweek night #1 $6,000 to win (RAIN Date of SUNDAY JUNE 13th) 410 Sprints - Winged: All Star Circuit of Champions Dirt Late Models | Results | | Ian Madsen (410 Sprints - Winged) | 3rd | 2nd | - | 1st |
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| 6/12/2021 | Fremont Speedway - Fremont, OH Ohio Sprint Speedweek night #2 $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Ian Madsen (410 Sprints - Winged) | 5th | - | 6th | 19th |
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| 6/14/2021 | Wayne County Speedway - Orrville, OH Ohio Sprint Speedweek night #3 $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Ian Madsen (410 Sprints - Winged) | 4th | - | - | 18th |
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| 6/15/2021 | Sharon Speedway - Hartford, OH Ohio Sprint Speedweek night #4 $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Ian Madsen (410 Sprints - Winged) | 4th | 2nd | - | 8th |
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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 | | Ian Madsen (410 Sprints - Winged) | 7th | - | 7th | - |
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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 | | Ian Madsen (410 Sprints - Winged) | 5th | - | - | 18th (DNF) |
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| 6/24/2021 | Jackson Motorplex - Jackson, MN AGCO Jackson Nationals - THE SHOWDOWN 410 Sprints - Winged: World of Outlaws | Results | | Ian Madsen (410 Sprints - Winged) | 7th | - | 7th | - |
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| 6/25/2021 | Jackson Motorplex - Jackson, MN AGCO Jackson Nationals - THE SHOWDOWN 410 Sprints - Winged: World of Outlaws | Results | | Ian Madsen (410 Sprints - Winged) | - | - | - | - |
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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 | | Ian Madsen (410 Sprints - Winged) | - | - | - | - |
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| 7/3/2021 | Knoxville Raceway - Knoxville, IA 360 Sprints - Winged, 410 Sprints - Winged, 305 Sprints - Winged | Results | | Ian Madsen (410 Sprints - Winged) | 4th | - | - | 21st |
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| 7/13/2021 | Attica Raceway Park - Attica, OH 410 Sprints - Winged: World of Outlaws | Results | | Ian Madsen (410 Sprints - Winged) | 11th (DNF) | - | - | - |
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| 7/14/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws | Results | | Ian Madsen (410 Sprints - Winged) | 2nd | 8th | - | 6th |
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| 7/15/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws | Results | | Ian Madsen (410 Sprints - Winged) | 5th | - | 7th | - |
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| 7/17/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws | Results | | Ian Madsen (410 Sprints - Winged) | 8th (DNF) | - | - | - |
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| 7/20/2021 | Lernerville Speedway - Sarver, PA 410 Sprints - Winged: World of Outlaws | Results | | Ian Madsen (410 Sprints - Winged) | 4th | - | - | 11th |
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| 8/6/2021 | Knoxville Raceway - Knoxville, IA 31st Annual ASCS 360 Knoxville Nationals 360 Sprints - Winged: ASCS National 410 Sprints - Winged, Winged Sprints | Results | | Ian Madsen (360 Sprints - Winged) | 2nd | - | - | 9th |
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| 8/7/2021 | Knoxville Raceway - Knoxville, IA 31st Annual ASCS 360 Knoxville Nationals 360 Sprints - Winged: ASCS National 410 Sprints - Winged, Winged Sprints | Results | | Ian Madsen (360 Sprints - Winged) | - | - | - | 23rd |
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| 8/12/2021 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged, Winged Sprints | Results | | Ian Madsen (410 Sprints - Winged) | 6th | - | 4th | 8th |
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| 8/14/2021 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged, Winged Sprints | Results | | Ian Madsen (410 Sprints - Winged) | - | - | - | 16th |
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| 8/20/2021 | I-96 Speedway - Lake Odessa, MI $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions B Modifieds, Street Stocks | Results | | Ian Madsen (410 Sprints - Winged) | 4th | 1st | - | 13th |
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| 8/21/2021 | Waynesfield Raceway Park - Waynesfield, OH 410 Sprints - Winged: All Star Circuit of Champions with FASTonDIRT 410 Sprints - Non-Winged: BOSS Buckeye Outlaw Sprint Series | Results | | Ian Madsen (410 Sprints - Winged) | 4th | - | - | 10th |
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| 8/26/2021 | Grandview Speedway - Bechtelsville, PA Thunder on the Hill $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Ian Madsen (410 Sprints - Winged) | 2nd | - | - | 12th |
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| 8/27/2021 | Williams Grove Speedway - Mechanicsburg, PA Jack Gunn Memorial - Twin 20s $4,000 to win each feature 410 Sprints - Winged: All Star Circuit of Champions | Rain Out |
| 8/28/2021 | Lincoln Speedway - Abbottstown, PA Kramer Klash $7,300 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Ian Madsen (410 Sprints - Winged) | 5th | - | - | 14th |
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| 8/29/2021 | BAPS Motor Speedway - York Haven, PA Johnny Mackison Clash $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions 305 Sprints - Winged | Results | | Ian Madsen (410 Sprints - Winged) | 6th | - | 1st | 12th |
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| 9/3/2021 | Attica Raceway Park - Attica, OH $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions Dirt Late Models | Results | | Ian Madsen (410 Sprints - Winged) | 8th (DNF) | - | DNS | 25th (DNF) |
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| 9/4/2021 | Attica Raceway Park - Attica, OH Attica Ambush $10,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Ian Madsen (410 Sprints - Winged) | 8th | - | 8th | - |
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| 9/9/2021 | Port Royal Speedway - Port Royal, PA $8,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Ian Madsen (410 Sprints - Winged) | 3rd | 4th | - | 12th |
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| 9/10/2021 | Port Royal Speedway - Port Royal, PA Night Before the 50 $10,000 to win 410 Sprints - Winged: All Star Circuit of Champions Dirt Super Late Models | Results | | Ian Madsen (410 Sprints - Winged) | 2nd | - | - | 17th |
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| 9/11/2021 | Port Royal Speedway - Port Royal, PA 54th annual Tuscarora 50 $54,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Ian Madsen (410 Sprints - Winged) | 2nd | - | - | 18th |
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| 9/17/2021 | Williams Grove Speedway - Mechanicsburg, PA Dirt Classic Qualifier $7,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Ian Madsen (410 Sprints - Winged) | 5th | - | - | 20th |
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| 9/18/2021 | Lincoln Speedway - Abbottstown, PA Dirt Classic $20,000 to win 410 Sprints - Winged: All Star Circuit of Champions | Results | | Ian Madsen (410 Sprints - Winged) | 8th | - | 10th | - |
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| 9/24/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws Midgets: USAC National Midgets Silver Crown: USAC Silver Crown | Results | | Ian Madsen (410 Sprints - Winged) | 1st | 4th | - | 16th |
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| 9/25/2021 | Eldora Speedway - Rossburg, OH 4 Crown Nationals $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions Midgets: USAC National Midgets 410 Sprints - Non-Winged: USAC National Sprint Cars Silver Crown: USAC Silver Crown 604 Crate Late Models | Results | | Ian Madsen (410 Sprints - Winged) | 3rd | - | - | 11th |
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