| | Heat | Dash | B Feature | A Feature |
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| 4/17/2021 | Beaver Dam Raceway - Beaver Dam, WI Wipperfurth Memorial 360 Sprints - Winged, Semi-Pro Legends | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 7th |
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| 4/24/2021 | Gravity Park Speedway - Chilton, WI 360 Sprints - Winged: MSA Sprint Car Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 7th |
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| 5/1/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 8th |
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| 5/7/2021 | Beaver Dam Raceway - Beaver Dam, WI 360 Sprints - Winged: MSA Sprint Car Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints Semi-Pro Legends | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 20th (DNF) |
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| 5/8/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association | Results | | Jack Vanderboom (360 Sprints - Winged) | (DNF) | - | DNS | - |
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| 5/15/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association | Results | | Jack Vanderboom (360 Sprints - Winged) | 8th | - | 5th | - |
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| 5/22/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 18th |
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| 5/29/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 11th |
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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 | | Jack Vanderboom (360 Sprints - Winged) | - | - | 10th | - |
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| 6/12/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 16th |
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| 6/18/2021 | Outagamie Speedway - Seymour, WI MSA Sprints join the program 360 Sprints - Winged: Midwest Sprint Car Association Street Stocks, IMCA Modified, IMCA Stock Car, IMCA Sport Compact | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 6th |
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| 6/25/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 7th |
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| 7/1/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI $5000 to win NASCAR Kick Off 360 Sprints - Winged: MSA Sprint Car Association 410 Sprints - Winged: IRA Interstate Racing Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 6th |
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| 7/10/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 4th |
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| 7/15/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 8th |
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| 7/23/2021 | Outagamie Speedway - Seymour, WI Fair Race 410 Sprints - Winged: IRA Interstate Racing Association IMCA Northern SportMod, IMCA Sport Compact | Results | | Jack Vanderboom (410 Sprints - Winged) | 5th | - | - | 14th |
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| 7/24/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 7th |
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| 7/30/2021 | Langlade County Speedway - Antigo, WI 410 Sprints - Winged: IRA Interstate Racing Association | Results | | Jack Vanderboom (410 Sprints - Winged) | 5th | - | - | 11th |
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| 7/31/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI Frank Filskov Memorial 360 Sprints - Winged: MSA Sprint Car Association 410 Sprints - Winged: IRA Interstate Racing Association Badger Midgets: Badger Midget Auto Racing Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | 9th | - | | Jack Vanderboom (410 Sprints - Winged) | 2nd | - | - | 18th |
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| 8/1/2021 | Angell Park Speedway - Sun Prairie, WI Non Wing Crate Sprints: Wisconsin wingLESS Sprints Badger Midgets: Badger Midget Auto Racing Association 360 Sprints - Winged, 410 Sprints - Winged | Results | | Jack Vanderboom (360 Sprints - Winged) | 1st | - | - | 7th |
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| 8/28/2021 | Beaver Dam Raceway - Beaver Dam, WI MSA 360 Sprint Cars, Legends and Street Stocks 360 Sprints - Winged: MSA Sprint Car Association Semi-Pro Legends | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 11th |
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| 9/4/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI Sheboygan County Fair 360 Sprints - Winged: MSA Sprint Car Association 410 Sprints - Winged: IRA Interstate Racing Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 3rd |
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| 9/11/2021 | Cedar Lake Speedway - New Richmond, WI Jerry Richert Memorial 360 Sprints - Winged: Midwest Power Series 410 Sprints - Winged: IRA Interstate Racing Association 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 305 Sprints - Non-Winged | Results | | Jack Vanderboom (410 Sprints - Winged) | 6th | - | - | 18th |
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| 9/18/2021 | Gravity Park Speedway - Chilton, WI 360 Sprints - Winged: MSA Sprint Car Association | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 16th |
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| 9/24/2021 | Dodge County Fairgrounds - Beaver Dam, WI Checkered Classic/Rick Schmidt Memorial 410 Sprints - Winged: IRA Interstate Racing Association Non Wing Crate Sprints: Wisconsin wingLESS Sprints 360 Sprints - Winged | Rain Out |
| 9/25/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI WI Sprint Car Championships 360 Sprints - Winged: MSA Sprint Car Association 410 Sprints - Winged: IRA Interstate Racing Association Lightning Sprints: IRA Lightning Sprints Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Jack Vanderboom (360 Sprints - Winged) | - | - | - | 1st |
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| 10/1/2021 | Beaver Dam Raceway - Beaver Dam, WI Non Wing Crate Sprints: Wisconsin wingLESS Sprints 360 Sprints - Winged, Semi-Pro Legends | Results | | Jack Vanderboom (360 Sprints - Winged) | 2nd | - | - | 6th |
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| 10/2/2021 | Beaver Dam Raceway - Beaver Dam, WI Non Wing Crate Sprints: Wisconsin wingLESS Sprints 360 Sprints - Winged, Semi-Pro Legends | Results | | Jack Vanderboom (360 Sprints - Winged) | 1st | - | - | 1st |
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