| | Heat | Dash | B Feature | A Feature |
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| 4/18/2014 | Cedar Lake Speedway Indoor Arena - New Richmond, WI Winged Points Winged A-Class: Miniakota Micro Sprint Series Generic 1 | Results | | Bill Boles (Winged A-Class) | - | - | - | 5th | | Bill Boles (Generic 1) | - | - | - | 5th |
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| 4/19/2014 | Cedar Lake Speedway Indoor Arena - New Richmond, WI Winged Points Winged A-Class: Miniakota Micro Sprint Series Generic 1 | Results | | Bill Boles (Winged A-Class) | - | - | - | 2nd | | Bill Boles (Generic 1) | - | - | - | 2nd |
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| 4/26/2014 | Jackson Motorplex - Jackson, MN 360 Sprints - Winged: JSTS - Jackson Speedway Touring Series Winged A-Class: Miniakota Micro Sprint Series Generic 1 | Results | | Bill Boles (360 Sprints - Winged) | - | - | - | 10th |
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| 5/17/2014 | Jackson Motorplex - Jackson, MN Nonwing opener. 360 Sprints - Winged: JSTS - Jackson Speedway Touring Series Stock Non-Wing, Generic 1 | Results | | Bill Boles (360 Sprints - Winged) | - | - | - | 7th |
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| 5/26/2014 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks, 360 Sprints - Non-Winged | Results | | Bill Boles (Winged Outlaw) | 2nd | - | - | 2nd |
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| 6/29/2014 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged, Hobby Stocks, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks | Results | | Bill Boles (Winged Outlaw) | 1st | - | - | 3rd |
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| 7/2/2014 | Huset's Speedway - Brandon, SD 410 Sprints - Winged: World of Outlaws Winged Outlaw, Winged A-Class, Street Stocks | Results | | Bill Boles (Winged Outlaw) | 2nd | - | - | 7th |
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| 7/3/2014 | Huset's Speedway - Brandon, SD July 3 Special - Outlaw Sprints & Fireworks! 410 Sprints - Winged, Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks | Results | | Bill Boles (Winged Outlaw) | 3rd | - | - | 6th |
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| 7/20/2014 | Huset's Speedway - Brandon, SD 410 Sprints - Winged: All Star Circuit of Champions Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks, 360 Sprints - Non-Winged | Results | | Bill Boles (Winged Outlaw) | 1st | - | - | 1st |
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| 7/27/2014 | Huset's Speedway - Brandon, SD Micro Sprint Car Racing 410 Sprints - Winged: All Star Circuit of Champions Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks, 360 Sprints - Non-Winged | Results | | Bill Boles (Winged Outlaw) | 2nd | - | - | 10th |
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| 8/3/2014 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks | Results | | Bill Boles (Winged Outlaw) | 3rd | - | - | 1st |
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| 8/8/2014 | Newcastle Speedway - Newcastle, WY Miniakota Vrs HMST Challenge race #2 Generic 1 | Results | | Bill Boles (Generic 1) | - | - | - | 19th |
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| 8/10/2014 | Huset's Speedway - Brandon, SD 360 Sprints - Winged, 410 Sprints - Winged, Hobby Stocks, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks | Results | | Bill Boles (Winged Outlaw) | 3rd | - | - | 14th (DNF) |
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| 8/31/2014 | Huset's Speedway - Brandon, SD Micro Sprint Car Racing 360 Sprints - Winged, 410 Sprints - Winged, Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks | Results | | Bill Boles (Winged Outlaw) | 2nd | - | - | 3rd |
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| 9/1/2014 | Huset's Speedway - Brandon, SD 360 Sprints - Winged: Minnesota Mafia Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks | Results | | Bill Boles (Winged Outlaw) | 1st | - | - | 1st |
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| 9/7/2014 | Huset's Speedway - Brandon, SD 410 Sprints - Winged, Hobby Stocks, Winged Outlaw, B Modifieds, Street Stocks | Results | | Bill Boles (Winged Outlaw) | 1st | - | - | 3rd |
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| 10/24/2014 | Cedar Lake Speedway Indoor Arena - New Richmond, WI Winged Points - 9th Annual Race4Life Winged A-Class: Miniakota Micro Sprint Series Non-Wing Outlaw, Stock Non-Wing, Generic 1 | Results | | Bill Boles (Winged A-Class) | - | - | - | 14th | | Bill Boles (Generic 1) | - | - | - | 6th |
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| 10/25/2014 | Cedar Lake Speedway Indoor Arena - New Richmond, WI Winged Points - 9th Annual Race4Life Winged A-Class: Miniakota Micro Sprint Series Non-Wing Outlaw, Stock Non-Wing, Generic 1 | Results | | Bill Boles (Winged A-Class) | - | - | - | 25th |
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| 12/30/2014 | Tulsa Expo Raceway - Tulsa, OK Move-in Economy Midgets, Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 1200cc Outlaws Non-Winged Minis | Results | | Bill Boles (Winged Outlaw) | - | - | - | - |
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