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| 1/29/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 2nd | - | - | 10th |
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| 1/30/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 8th (DNF) | - | DNS | - |
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| 2/2/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 3rd | 1st | - | 2nd |
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| 2/3/2021 | DIRTcar Nationals $6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 2nd | - | - | 19th |
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| 2/4/2021 | DIRTcar Nationals $6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 2nd | - | - | 19th |
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| 2/5/2021 | 50th Annual DIRTcar Nationals - Night #4 (DIRTcar UMP Modifieds Gator Championship Night 1) | Results | | Ian Madsen (410 Winged Sprints) | 8th (DNF) | - | DNS | - |
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| 3/12/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 5th | - | - | 10th |
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| 3/13/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 3rd | - | - | 8th |
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| 3/19/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 2nd | 3rd | - | 4th |
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| 3/20/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 6th | - | - | 13th |
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| 3/27/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 5th | - | - | 13th |
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| 4/3/2021 | Core and Main Spring Nationals $6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 3rd | 4th | - | 8th |
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| 4/9/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 1st | 8th | - | 4th |
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| 4/10/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 1st | 4th | - | 10th |
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| 4/15/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 3rd | 2nd | - | 17th (DNF) |
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| 4/16/2021 | The Tommy Hinnershitz Classic -$6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 1st | 2nd | - | 4th |
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| 4/17/2021 | Keith Kauffman Classic $10,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 3rd | 3rd | - | 3rd |
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| 4/18/2021 | Johnny Grum Classic $6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 3rd | 7th | - | 8th |
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| 4/24/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 2nd | - | - | 2nd |
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| 5/1/2021 | Buckeye Cup $6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 2nd | 2nd | - | 3rd |
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| 5/2/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 4th | 1st | - | 3rd |
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| 5/7/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 3rd | - | - | 6th |
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| 5/8/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 1st | 1st | - | 4th |
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| 5/14/2021 | Mace Thomas Classic - $8,500 to win | Results | | Ian Madsen (410 Winged Sprints) | 4th | 1st | - | 2nd |
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| 5/15/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 3rd | - | - | 7th |
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| 5/20/2021 | All Star Indiana Invasion presented by Rayce Rudeen Foundation $6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 2nd | 5th | - | 10th |
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| 5/21/2021 | All Star Indiana Invasion presented by Rayce Rudeen Foundation $10,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 3rd | - | - | 16th |
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| 5/22/2021 | All Star Indiana Invasion presented by Rayce Rudeen Foundation $6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 6th | - | 2nd | 17th |
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| 5/23/2021 | All Star Indiana Invasion presented by Rayce Rudeen Foundation $26,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 1st | 6th | - | 24th (DNF) |
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Watch on FloRacing05/31/21 4:00 PM EST Click the icon to go to broadcast | 5/31/2021 | Bob Weikert Memorial $29,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 2nd | - | - | 10th |
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Watch on FloRacing06/03/21 6:00 PM CST Click the icon to go to broadcast | 6/3/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 1st | 4th | - | 4th |
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Watch on FloRacing06/04/21 6:00 PM CST Click the icon to go to broadcast | 6/4/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 4th | 1st | - | 2nd |
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Watch on FloRacing06/05/21 5:30 PM CST Click the icon to go to broadcast | 6/5/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 2nd | 1st | - | 2nd |
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Watch on FloRacing06/06/21 6:30 PM CST Click the icon to go to broadcast | 6/6/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 4th | 5th | - | 2nd |
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Watch on FloRacing06/11/21 6:30 PM CST Click the icon to go to broadcast | 6/11/2021 | Ohio Sprint Speedweek night #1 $6,000 to win (RAIN Date of SUNDAY JUNE 13th) | Results | | Ian Madsen (410 Winged Sprints) | 3rd | 2nd | - | 1st |
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| 6/12/2021 | Ohio Sprint Speedweek night #2 $6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 5th | - | 6th | 19th |
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| 6/14/2021 | Ohio Sprint Speedweek night #3 $6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 4th | - | - | 18th |
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| 6/15/2021 | Ohio Sprint Speedweek night #4 $6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 4th | 2nd | - | 8th |
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Watch on DIRTVision06/21/21 7:00 PM CST Click the icon to go to broadcast | 6/21/2021 | The SHOWDOWN -HUSET'S 50 presented by BillionAuto.com | Results | | Ian Madsen (410 Winged Sprints) | 7th | - | 7th | - |
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Watch on DIRTVision06/22/21 7:00 PM CST Click the icon to go to broadcast | 6/22/2021 | THE SHOWDOWN - HUSET'S 50 - presented by BillionAuto.com | Results | | Ian Madsen (410 Winged Sprints) | 5th | - | - | 18th (DNF) |
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| 6/24/2021 | AGCO Jackson Nationals - THE SHOWDOWN | Results | | Ian Madsen (410 Winged Sprints) | 7th | - | 7th | - |
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| 6/25/2021 | AGCO Jackson Nationals - THE SHOWDOWN | Results | | Ian Madsen (410 Winged Sprints) | - | - | - | - |
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| 6/26/2021 | AGCO Jackson Nationals - THE SHOWDOWN | Postponed |
| 6/27/2021 | 43rd Annual AGCO Jackson Nationals | Results | | Ian Madsen (410 Winged Sprints) | - | - | - | - |
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| 7/3/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 4th | - | - | 21st |
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| 7/13/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 11th (DNF) | - | - | - |
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| 7/14/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 2nd | 8th | - | 6th |
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| 7/15/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 5th | - | 7th | - |
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| 7/17/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 8th (DNF) | - | - | - |
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| 7/20/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 4th | - | - | 11th |
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| 8/6/2021 | 31st Annual ASCS 360 Knoxville Nationals | Results | | Ian Madsen (360 Winged Sprints) | 2nd | - | - | 9th |
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| 8/7/2021 | 31st Annual ASCS 360 Knoxville Nationals | Results | | Ian Madsen (360 Winged Sprints) | - | - | - | 23rd |
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| 8/12/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 6th | - | 4th | 8th |
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| 8/14/2021 | | Results | | Ian Madsen (410 Winged Sprints) | - | - | - | 16th |
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| 8/20/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 4th | 1st | - | 13th |
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| 8/21/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 4th | - | - | 10th |
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| 8/26/2021 | Thunder on the Hill $6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 2nd | - | - | 12th |
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| 8/27/2021 | Jack Gunn Memorial - Twin 20s $4,000 to win each feature | Rain Out |
| 8/28/2021 | Kramer Klash $7,300 to win | Results | | Ian Madsen (410 Winged Sprints) | 5th | - | - | 14th |
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| 8/29/2021 | Johnny Mackison Clash $5,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 6th | - | 1st | 12th |
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| 9/3/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 8th (DNF) | - | DNS | 25th (DNF) |
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| 9/4/2021 | Attica Ambush $10,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 8th | - | 8th | - |
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| 9/9/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 3rd | 4th | - | 12th |
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| 9/10/2021 | Night Before the 50 $10,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 2nd | - | - | 17th |
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| 9/11/2021 | 54th annual Tuscarora 50 $54,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 2nd | - | - | 18th |
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| 9/17/2021 | Dirt Classic Qualifier $7,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 5th | - | - | 20th |
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| 9/18/2021 | Dirt Classic $20,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 8th | - | 10th | - |
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| 9/24/2021 | | Results | | Ian Madsen (410 Winged Sprints) | 1st | 4th | - | 16th |
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| 9/25/2021 | 4 Crown Nationals $6,000 to win | Results | | Ian Madsen (410 Winged Sprints) | 3rd | - | - | 11th |
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