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| 4/26/2019 | Red Cedar Speedway - Menomonie, WI Red Cedar Speedway GIve Back to Charity Night DIRTcar UMP Modifieds, Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Ben Hillman (WISSOTA Super Stock) | DNS | - | - | DNS |
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| 6/21/2019 | Red Cedar Speedway - Menomonie, WI Race Of Champion Qualifier Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Ben Hillman (WISSOTA Super Stock) | 4th | - | - | 16th (DNF) |
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| 6/29/2019 | Cedar Lake Speedway - New Richmond, WI CLS Dash Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Ben Hillman (Super Stocks) | 4th | - | - | 5th |
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| 7/12/2019 | Red Cedar Speedway - Menomonie, WI Military Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Ben Hillman (WISSOTA Super Stock) | 4th | - | - | 3rd |
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| 7/13/2019 | Rice Lake Speedway - Rice Lake, WI AFCO Race of Champions Qualifers, Rain Date Aug. 10 DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Ben Hillman (WISSOTA Street Stock) | 4th | - | - | 17th (DNF) | | Ben Hillman (WISSOTA Super Stock) | 3rd | - | - | 6th |
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| 7/25/2019 | Red Cedar Speedway - Menomonie, WI Dunn County Fair Night #1 Dirt Super Late Models, Hornets, WISSOTA Late Model, WISSOTA Street Stock | Results | | Ben Hillman (WISSOTA Street Stock) | 6th | - | - | 17th (DNF) |
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| 7/26/2019 | Red Cedar Speedway - Menomonie, WI Dunn County Fair Night #2 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Ben Hillman (WISSOTA Super Stock) | 1st | - | - | 2nd |
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| 7/30/2019 | Rice Lake Speedway - Rice Lake, WI 25th Annual Street Stock Little Dream WISSOTA Street Stock | Results | | Ben Hillman (WISSOTA Street Stock) | 1st | - | 2nd | 22nd (DNF) |
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| 8/9/2019 | Red Cedar Speedway - Menomonie, WI Regular Race Night/ROC Raindate Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Ben Hillman (WISSOTA Super Stock) | 3rd | - | - | 6th |
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| 8/16/2019 | Red Cedar Speedway - Menomonie, WI 3rd Annual Mahder 55 Wissota Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series Dirt Super Late Models, WISSOTA Modifieds, WISSOTA Super Stock | Results | | Ben Hillman (WISSOTA Super Stock) | 3rd | - | - | 5th |
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| 8/30/2019 | Red Cedar Speedway - Menomonie, WI Championship Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Ben Hillman (WISSOTA Super Stock) | 5th | - | - | 5th |
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| 9/20/2019 | Red Cedar Speedway - Menomonie, WI 40th Annual Punky Manor Challenge Of Champions Heat Races DIRTcar UMP Modifieds, A Modifieds, B Modifieds, Dirt Late Models, Super Stocks, WISSOTA Modifieds | Results | | Ben Hillman (Super Stocks) | 4th | - | - | - |
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| 9/21/2019 | Red Cedar Speedway - Menomonie, WI 40th Annual Punky Manor Challenge Of Champions Night #3 Features DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Ben Hillman (WISSOTA Super Stock) | 4th | - | - | 8th |
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