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| 5/22/2016 | Angell Park Speedway - Sun Prairie, WI 410 Sprints - Winged: IRA Interstate Racing Association Winged A-Class: Badger 600 Winged Micros Badger Midgets: Badger Midget Auto Racing Association Winged Outlaw | Results | | Jack Vanderboom (Winged A-Class) | 5th | - | - | 6th |
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| 6/11/2016 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association Winged Outlaw: Midwest Micro Sprints Winged A-Class | Results | | Jack Vanderboom (Winged Outlaw) | 4th | - | - | 6th | | Jack Vanderboom (Winged A-Class) | 4th | - | - | 6th |
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| 7/9/2016 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association Winged Outlaw: Midwest Micro Sprints Badger Midgets: Badger Midget Auto Racing Association Winged A-Class | Results | | Jack Vanderboom (Winged Outlaw) | 4th | - | - | 6th | | Jack Vanderboom (Winged A-Class) | 4th | - | - | 4th |
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| 7/31/2016 | Angell Park Speedway - Sun Prairie, WI Winged A-Class: Badger 600 Winged Micros Non Wing Crate Sprints: Wisconsin wingLESS Sprints Badger Midgets: Badger Midget Auto Racing Association Winged Outlaw, Pro Legends, Masters Legends | Results | | Jack Vanderboom (Winged Outlaw) | 4th | - | - | 9th | | Jack Vanderboom (Winged A-Class) | 4th | - | - | 9th |
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| 8/6/2016 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI 360 Sprints - Winged: MSA Sprint Car Association 410 Sprints - Winged: IRA Interstate Racing Association Winged Outlaw: Midwest Micro Sprints Winged A-Class: Badger 600 Winged Micros | Results | | Jack Vanderboom (Winged Outlaw) | 6th | - | - | 5th | | Jack Vanderboom (Winged A-Class) | 6th | - | - | 5th |
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| 8/14/2016 | Angell Park Speedway - Sun Prairie, WI 360 Sprints - Winged: MSA Sprint Car Association Winged A-Class: Badger 600 Winged Micros Non Wing Crate Sprints: Wisconsin wingLESS Sprints Badger Midgets: Badger Midget Auto Racing Association Winged Outlaw, Pro Legends, Masters Legends | Results | | Jack Vanderboom (Winged Outlaw) | 4th | - | - | 6th | | Jack Vanderboom (Winged A-Class) | 4th | - | - | 6th |
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| 8/20/2016 | Sycamore Speedway - Sycamore, IL Winged A-Class: Badger 600 Winged Micros Winged Outlaw | Results | | Jack Vanderboom (Winged A-Class) | 2nd | - | - | 2nd |
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| 9/4/2016 | Angell Park Speedway - Sun Prairie, WI The Kevin Doty Classic Winged A-Class: Badger 600 Winged Micros 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Non Wing Crate Sprints: Wisconsin wingLESS Sprints Badger Midgets: Badger Midget Auto Racing Association Winged Outlaw | Results | | Jack Vanderboom (Winged Outlaw) | 6th | - | - | 10th | | Jack Vanderboom (Winged A-Class) | 6th | - | - | 10th |
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