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| 3/23/2019 | Highland Speedway - Highland, IL Lucky 40 DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Jeb Simmons (B Modifieds) | - | - | - | - |
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| 5/17/2019 | Tri City Speedway - Granite City, IL Midgets: USAC National Midgets 410 Sprints - Non-Winged: USAC National Sprint Cars B Modifieds, Non-Winged Sprints | Results | | Jeb Simmons (B Modifieds) | 4th | - | - | 18th |
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| 5/18/2019 | Tri City Speedway - Granite City, IL Rivertown Showdown Night #2 - USAC Sprints & USAC Midgets & B Modifieds Midgets, B Modifieds, 410 Sprints - Non-Winged, Non-Winged Sprints | Results | | Jeb Simmons (B Modifieds) | 7th | - | - | - |
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| 5/31/2019 | Tri City Speedway - Granite City, IL UMP vs AMS Mods $2000/B-Modifieds $1000/UMP Crate Late Models $1000/UMP St. Stocks $250/Kidz Modz DIRTcar UMP Modifieds, B Modifieds, Street Stocks, Generic 1, Pro Late Model | Results | | Jeb Simmons (B Modifieds) | 6th (DNF) | - | 10th | - |
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| 9/6/2019 | Tri City Speedway - Granite City, IL Brad Yotter Memorial - UMP Late Models/UMP Mods/B-Mods/UMP Crate LM/Street Stock/Wing Micros DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Jeb Simmons (DIRTcar Late Models) | 6th | - | - | 9th |
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| 12/19/2019 | The Dome at America's Center - St. Louis, MO 4th annual Arizona Sport Shirts Gateway Dirt Nationals presented by O’Reilly Auto Parts Midgets, Dirt Super Late Models, A Modifieds | Results | | Jeb Simmons (Dirt Super Late Models) | - | - | - | - |
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| 12/20/2019 | The Dome at America's Center - St. Louis, MO 4th annual Arizona Sport Shirts Gateway Dirt Nationals presented by O’Reilly Auto Parts Midgets, Dirt Super Late Models, A Modifieds | Results | | Jeb Simmons (Dirt Super Late Models) | 7th | - | - | - |
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| 12/21/2019 | The Dome at America's Center - St. Louis, MO 4th annual Arizona Sport Shirts Gateway Dirt Nationals presented by O’Reilly Auto Parts Midgets, Dirt Super Late Models, A Modifieds | Results | | Jeb Simmons (Dirt Super Late Models) | - | - | 9th (DNF) | - |
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