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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 | | Chris Sleep (250 Winged Outlaw) | 1st | - | - | 3rd |
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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 | | Chris Sleep (250 Winged Outlaw) | 2nd | - | - | 4th |
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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 | | Chris Sleep (250 Winged Outlaw) | 1st | - | - | 1st |
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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 | | Chris Sleep (250 Winged Outlaw) | 3rd | - | - | 2nd |
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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 | | Chris Sleep (250 Winged Outlaw) | 6th | - | - | 3rd |
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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 | | Chris Sleep (250 Winged Outlaw) | 4th | - | - | 6th |
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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 | | Chris Sleep (250 Winged Outlaw) | 4th | - | - | 2nd |
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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 | | Chris Sleep (250 Winged Outlaw) | 2nd | - | - | 1st |
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| 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 | | Chris Sleep (250 Winged Outlaw) | 3rd | - | - | 4th |
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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 | | Chris Sleep (250 Winged Outlaw) | 5th | - | - | 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 | | Chris Sleep (250 Winged Outlaw) | 1st | - | - | 1st |
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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 | | Chris Sleep (250 Winged Outlaw) | 4th | - | - | 4th |
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| 9/19/2019 | Red Cedar Speedway - Menomonie, WI 40th Annual Punky Manor Night #1 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Dirt Super Late Models, Hornets, WISSOTA Pure Stock, WISSOTA Street Stock | Results | | Chris Sleep (Hornets) | 5th | - | - | 7th |
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