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| 5/3/2014 | Cedar Lake Speedway - New Richmond, WI 6th Annual Spring Sprint Special 360 Sprints - Winged | Results | | Anna Kouba (360 Sprints - Winged) | 5th | 7th | - | 13th |
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| 5/17/2014 | North Central Speedway - Brainerd, MN Spring Sprint Show 360 Sprints - Winged | Results | | Anna Kouba (360 Sprints - Winged) | 3rd | 4th | - | 12th (DNF) |
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| 5/24/2014 | Rice Lake Speedway - Rice Lake, WI 2nd Annual Double Dare Sprint Special 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 360 Sprints - Winged | Results | | Anna Kouba (360 Sprints - Winged) | 5th | 4th | - | 7th |
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| 6/6/2014 | Princeton Speedway - Princeton, MN 13th Annual Billy Anderson Memorial 360 Sprints - Winged | Results | | Anna Kouba (360 Sprints - Winged) | 4th | 4th | - | 12th |
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| 7/5/2014 | Hibbing Speedway - Hibbing, MN 2nd Annual Northern Tour (4th Ann. Rumble on the Range) 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 360 Sprints - Winged | Results | | Anna Kouba (360 Sprints - Winged) | 6th | 6th | - | 9th |
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| 7/6/2014 | Proctor Speedway - Proctor, MN 2nd Annual Northern Tour 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 360 Sprints - Winged | Results | | Anna Kouba (360 Sprints - Winged) | 5th | 4th | - | 6th |
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| 7/20/2014 | Granite City Motor Park - Sauk Rapids, MN 3rd Annual Granite City Sprintacular 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 360 Sprints - Winged | Results | | Anna Kouba (360 Sprints - Winged) | 5th | 3rd | - | 14th (DNF) |
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| 7/26/2014 | Cedar Lake Speedway - New Richmond, WI Summer Sprint Special 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 360 Sprints - Winged | Results | | Anna Kouba (360 Sprints - Winged) | 5th | 7th | - | 15th (DNF) |
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| 8/9/2014 | Ogilvie Raceway - Ogilvie, MN August Heat Sprint Special 360 Sprints - Winged | Results | | Anna Kouba (360 Sprints - Winged) | 3rd | 3rd | - | 5th |
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| 8/15/2014 | Princeton Speedway - Princeton, MN 22nd Annual (Ethel) Kouba Memorial 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 360 Sprints - Winged | Results | | Anna Kouba (360 Sprints - Winged) | 6th (DNF) | 7th (DNF) | - | 15th (DNF) | | Anna Kouba (360 Sprints - Non-Winged) | 8th | - | - | 10th |
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| 8/30/2014 | North Central Speedway - Brainerd, MN 13th Annual Mighty Axe Nationals 360 Sprints - Winged | Results | | Anna Kouba (360 Sprints - Winged) | DNS | 5th | - | 6th |
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| 8/31/2014 | North Central Speedway - Brainerd, MN 13th Annual Mighty Axe Nationals 360 Sprints - Winged | Results | | Anna Kouba (360 Sprints - Winged) | 1st | - | - | 7th |
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| 9/5/2014 | St. Croix Speedway - St. Croix Falls, WI 22nd Annual (Earl) Kouba Memorial Winged Outlaw: Minnesota Micro Sprints 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 360 Sprints - Winged, DIRTcar Sport Compact, Factory Stocks, Stock Cars, Winged A-Class, Vintage Full Body Stock Cars, Vintage Modifieds | Results | | Anna Kouba (360 Sprints - Winged) | 5th | 7th | - | 21st (DNF) |
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| 9/6/2014 | Cedar Lake Speedway - New Richmond, WI 410 Sprints - Winged: IRA Interstate Racing Association Vintage Modifieds: Northern Vintage Stockcar Racers 360 Sprints - Winged, Vintage Full Body Stock Cars | Results | | Anna Kouba (360 Sprints - Winged) | 4th | 9th (DNF) | - | 10th |
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