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| 5/5/2019 | Thunder Hill Speedway - Menomonie, WI Open Practice! Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | - | - | - | - |
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| 5/12/2019 | Thunder Hill Speedway - Menomonie, WI Open Practice! Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | - | - | - | - |
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| 5/15/2019 | Thunder Hill Speedway - Menomonie, WI Racing All Access Night! Season Opener! Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | 4th | - | - | 6th | | Ashley Williams (Junior Sportsman Dirt Karts) | 2nd | - | - | 5th |
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| 5/24/2019 | Princeton Speedway - Princeton, MN Meet the Drivers Night Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | 4th | - | - | 6th |
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| 5/29/2019 | Thunder Hill Speedway - Menomonie, WI Synergy Co-op Night Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | 3rd | - | - | 7th | | Ashley Williams (Junior Sportsman Dirt Karts) | 2nd | - | - | 3rd |
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| 6/5/2019 | Thunder Hill Speedway - Menomonie, WI D & J Mini Warehouse Night Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | 4th | - | - | 3rd | | Ashley Williams (Junior Sportsman Dirt Karts) | 2nd | - | - | 1st |
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| 6/7/2019 | Princeton Speedway - Princeton, MN Bike Giveaway Night Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | 5th | - | - | 10th |
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| 6/8/2019 | Granite City Motor Park - Sauk Rapids, MN 410 Sprints - Winged: World of Outlaws Winged A-Class, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | 5th | - | - | 9th |
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| 6/12/2019 | Thunder Hill Speedway - Menomonie, WI Cody Plumbing Night! Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | 1st | - | - | 7th | | Ashley Williams (Junior Sportsman Dirt Karts) | 2nd | - | - | 4th |
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| 6/19/2019 | Thunder Hill Speedway - Menomonie, WI Red Cedar Speedway Night! Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | 1st | - | - | 12th | | Ashley Williams (Junior Sportsman Dirt Karts) | 1st | - | - | 1st |
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| 6/21/2019 | Princeton Speedway - Princeton, MN Afco race of champions for Supers and Mod 4s Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | 5th | - | - | 8th |
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| 6/22/2019 | North Central Speedway - Brainerd, MN Weekly racing presented by Cub Foods Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | 2nd | - | - | 4th |
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| 6/23/2019 | Granite City Motor Park - Sauk Rapids, MN Micro Sprints Winged A-Class, Stock Non-Wing, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Super Stock, WISSOTA Hornet | Rain Out |
| 6/30/2019 | Thunder Hill Speedway - Menomonie, WI Pre-Nationals Open Practice Winged A-Class, Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | - | - | - | - |
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| 7/3/2019 | Thunder Hill Speedway - Menomonie, WI 2019 Advance Auto Parts Outlaw Kart Nationals! Night 1 Winged A-Class, Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (Winged A-Class) | 1st | - | - | 7th | | Ashley Williams (500 Winged Open Outlaw) | - | - | - | - | | Ashley Williams (Junior Sportsman Dirt Karts) | 2nd | - | - | 5th |
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| 7/4/2019 | Thunder Hill Speedway - Menomonie, WI 2019 Advance Auto Parts Outlaw Kart Nationals! Night 2! Winged A-Class, Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (Winged A-Class) | 2nd | - | - | 3rd | | Ashley Williams (500 Winged Open Outlaw) | - | - | - | - | | Ashley Williams (Junior Sportsman Dirt Karts) | 5th | - | - | 5th |
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| 7/5/2019 | Princeton Speedway - Princeton, MN Bottle Rocket Spectacular Day 2 Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | 3rd | - | - | 5th |
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| 7/17/2019 | Thunder Hill Speedway - Menomonie, WI Otter Acres Plaques and Trophies Night! Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | 4th | - | - | 4th | | Ashley Williams (Junior Sportsman Dirt Karts) | 2nd | - | - | 4th |
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| 7/19/2019 | Princeton Speedway - Princeton, MN Fight to the Finish Night Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Dwarf, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Rain Out |
| 7/31/2019 | Thunder Hill Speedway - Menomonie, WI T & T Construction Night! Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | 4th | - | - | 10th | | Ashley Williams (Junior Sportsman Dirt Karts) | 1st | - | - | 1st |
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| 8/2/2019 | Princeton Speedway - Princeton, MN Hobby Stock Tour Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | 6th | - | - | 7th |
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| 8/9/2019 | Princeton Speedway - Princeton, MN Back to School Night by Viking Coke Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | 4th | - | - | 12th (DNF) |
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| 8/10/2019 | North Central Speedway - Brainerd, MN Back to School Night by Viking Coke Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | 3rd | - | - | 6th |
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| 8/11/2019 | Granite City Motor Park - Sauk Rapids, MN Micro Sprints Winged A-Class, Stock Non-Wing, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Super Stock, WISSOTA Hornet | Results | | Ashley Williams (Winged A-Class) | - | - | - | - |
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| 8/14/2019 | Thunder Hill Speedway - Menomonie, WI Bill's Distributing Night! Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | 6th | - | - | 11th | | Ashley Williams (Junior Sportsman Dirt Karts) | 2nd | - | - | 3rd |
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| 8/21/2019 | Thunder Hill Speedway - Menomonie, WI Timber Inn Bar & Grill Night! Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | - | - | - | - | | Ashley Williams (Junior Sportsman Dirt Karts) | 2nd | - | - | 2nd |
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| 8/28/2019 | Thunder Hill Speedway - Menomonie, WI Dunn Energy Co-op Night! Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | - | - | - | - | | Ashley Williams (Junior Sportsman Dirt Karts) | 3rd | - | - | 2nd |
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| 8/30/2019 | Princeton Speedway - Princeton, MN Season championship Night Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | DNS | - | - | 11th |
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| 8/31/2019 | North Central Speedway - Brainerd, MN Mighty axe nationals Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | 6th | - | - | 8th |
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| 9/1/2019 | North Central Speedway - Brainerd, MN Mighty axe nationals Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | 5th | - | - | 11th |
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| 9/6/2019 | Thunder Hill Speedway - Menomonie, WI Advance Auto Parts Night before the 2019 WI Dirt Track State Championships Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | - | - | - | - |
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| 9/7/2019 | Thunder Hill Speedway - Menomonie, WI 2019 WI DIRT TRACK STATE CHAMPIONSHIPS! Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Rain Out |
| 9/21/2019 | Princeton Speedway - Princeton, MN Ptown Showdown Hobby Stocks, A Modifieds, Winged A-Class, B Modifieds, Sport Compact, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Ashley Williams (Winged A-Class) | 5th | - | - | 8th |
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| 10/4/2019 | Thunder Hill Speedway - Menomonie, WI KING OF THE HILL 100 Winged A-Class, Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | - | - | - | - |
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| 10/5/2019 | Thunder Hill Speedway - Menomonie, WI 2019 WI Dirt Track State Championships Rookie Class, 250 Winged Outlaw, 500 Winged Open Outlaw, Junior Sportsman Dirt Karts, Cage Jr. 206 A | Results | | Ashley Williams (500 Winged Open Outlaw) | - | - | - | - |
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| 10/12/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO ShowMe Showdown in Honor of Dean Hathman Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Ashley Williams (Winged Outlaw) | 6th | - | 11th | 18th | | Ashley Williams (Winged A-Class) | 8th | - | 9th | - |
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