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| 5/28/2023 | Kokomo Speedway - Kokomo, IN BC's Indiana Double Hobby Stocks, A Modifieds, 410 Sprints - Non-Winged | Results | | Jeffery Jessup (A Modifieds) | DNS | - | DNS | - |
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| 6/2/2023 | Limaland Motorsports Park - Lima, OH 21st Annual Keyser Memorial 410 Sprints - Non-Winged: Great Lakes Traditional Sprints DIRTcar UMP Modifieds, Stock Cars, Dirt Pro Trucks | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 4th | - | - | 10th |
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| 6/9/2023 | Limaland Motorsports Park - Lima, OH Ron Kale Jr Memorial 360 Sprints - Winged: NRA Sprint Invaders DIRTcar UMP Modifieds, Stock Cars | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 2nd | - | - | 7th |
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| 6/16/2023 | Limaland Motorsports Park - Lima, OH Family Fun Night - Presented by University of Northwestern Ohio Midgets, DIRTcar UMP Modifieds, Stock Cars, Dirt Pro Trucks | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 4th | - | - | 10th |
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| 6/23/2023 | Limaland Motorsports Park - Lima, OH Tribute to Mr Excitement, Tim Allison 360 Sprints - Winged: NRA Sprint Invaders DIRTcar UMP Modifieds, Stock Cars, Winged Outlaw | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 2nd | - | - | 14th |
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| 6/24/2023 | Montpelier Motor Speedway - Montpelier, IN DIRTcar UMP Modifieds, Dirt Mini Trucks, Street Stocks, Hornets, Super Stocks | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | - | - | - | - |
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| 7/3/2023 | Kokomo Speedway - Kokomo, IN Fireworks Show Hobby Stocks, A Modifieds, 410 Sprints - Non-Winged | Results | | Jeffery Jessup (A Modifieds) | 6th | - | 10th | - |
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| 7/8/2023 | Montpelier Motor Speedway - Montpelier, IN Midgets: USAC Midwest Thunder Speed2 Midgets DIRTcar UMP Modifieds, Dirt Mini Trucks, Street Stocks, Hornets, Super Stocks | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 1st | - | - | - |
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| 7/13/2023 | Butler Speedway - Quincy, MI DIRTcar Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 8th | - | 7th | - |
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| 7/14/2023 | Limaland Motorsports Park - Lima, OH Meet the Drivers Night 360 Sprints - Winged: NRA Sprint Invaders DIRTcar UMP Modifieds, Stock Cars, Winged Outlaw | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 6th | - | 4th | 16th |
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| 7/15/2023 | Circle City Raceway - Indianapolis, IN 2nd Annual Crossroads Classic Indiana Racesaver Winged Sprints IMCA RaceSaver Sprint Car: Indiana Racesaver Sprints DIRTcar UMP Modifieds, Non-Wing Outlaw, Pro Legends, Hornets | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | DNS | - | - | DNS | | Jeffery Jessup (Pro Legends) | - | - | - | - |
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| 7/21/2023 | Limaland Motorsports Park - Lima, OH K & L Ready Mix Clash 360 Sprints - Winged: NRA Sprint Invaders DIRTcar UMP Modifieds, Stock Cars, Winged Outlaw | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 6th | - | 4th | - |
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| 7/22/2023 | Montpelier Motor Speedway - Montpelier, IN In memory of John Halsey DIRTcar UMP Modifieds, Dirt Mini Trucks, Street Stocks, Hornets, Super Stocks, Crown Vic | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | - | - | - | - |
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| 7/28/2023 | Limaland Motorsports Park - Lima, OH 26th Annual Championship Night 410 Sprints - Non-Winged: Great Lakes Traditional Sprints DIRTcar UMP Modifieds, Stock Cars | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 5th | - | - | 24th |
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| 7/29/2023 | Montpelier Motor Speedway - Montpelier, IN DIRTcar UMP Modifieds, Street Stocks, Hornets, Super Stocks | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 7th | - | - | 10th |
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| 8/5/2023 | Montpelier Motor Speedway - Montpelier, IN DIRTcar UMP Modifieds, Street Stocks, Hornets, Super Stocks, Crown Vic | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 3rd | - | - | - |
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| 8/19/2023 | Montpelier Motor Speedway - Montpelier, IN DIRTcar UMP Modifieds, Dirt Mini Trucks, Street Stocks, Hornets, Super Stocks | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 6th | - | - | 9th |
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| 8/26/2023 | Montpelier Motor Speedway - Montpelier, IN Midgets, DIRTcar UMP Modifieds, Street Stocks, Hornets, Super Stocks | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | - | - | - | 23rd |
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| 9/2/2023 | Montpelier Motor Speedway - Montpelier, IN Dirt Super Late Models, DIRTcar Late Models, DIRTcar UMP Modifieds, Non-Winged Sprints, Hornets | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 6th | - | 5th | - |
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| 9/3/2023 | Kokomo Speedway - Kokomo, IN Vince Osman Championship & Fireworks DIRTcar UMP Modifieds, Hobby Stocks, A Modifieds, 410 Sprints - Non-Winged | Results | | Jeffery Jessup (A Modifieds) | 5th | - | 3rd | - |
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| 9/9/2023 | Montpelier Motor Speedway - Montpelier, IN DIRTcar UMP Modifieds, Street Stocks, Hornets, Super Stocks, Crown Vic | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | - | - | - | - |
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| 9/15/2023 | Circle City Raceway - Indianapolis, IN USAC NATIONAL AMSOIL SPRINT CAR NATIONAL CHAMPIONSHIP Midgets: USAC Midwest Thunder Speed2 Midgets 410 Sprints - Non-Winged: USAC National Sprint Cars DIRTcar UMP Modifieds | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 7th | - | - | 22nd |
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| 9/16/2023 | Montpelier Motor Speedway - Montpelier, IN Midgets, DIRTcar UMP Modifieds, Street Stocks, Hornets, Super Stocks | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | - | - | - | - |
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| 9/22/2023 | Montpelier Motor Speedway - Montpelier, IN Speed Fest 2023 DIRTcar Late Models, DIRTcar UMP Modifieds, Non-Wing Outlaw, Hornets, Crown Vic | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | - | - | - | - |
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| 9/23/2023 | Montpelier Motor Speedway - Montpelier, IN Speed Fest 2023 DIRTcar Late Models, DIRTcar UMP Modifieds, Dirt Mini Trucks, Street Stocks, Hornets, Super Stocks | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | - | - | - | - |
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| 9/30/2023 | Montpelier Motor Speedway - Montpelier, IN 410 Sprints - Non-Winged: BOSS Buckeye Outlaw Sprint Series DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks, Hornets | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | - | - | - | - |
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| 10/7/2023 | Montpelier Motor Speedway - Montpelier, IN DIRTcar UMP Modifieds, Street Stocks, Hornets, Super Stocks, Crown Vic | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | - | - | - | - |
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| 10/14/2023 | Kokomo Speedway - Kokomo, IN Kokomo Klash XVII Dirt Super Late Models, A Modifieds, Street Stocks, Hornets | Postponed |
| 10/15/2023 | Kokomo Speedway - Kokomo, IN Kokomo Klash XVII **Rain Date** Dirt Super Late Models, DIRTcar UMP Modifieds, Street Stocks, Hornets | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | 9th | - | 4th | - |
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| 10/21/2023 | Montpelier Motor Speedway - Montpelier, IN DIRTcar UMP Modifieds, Street Stocks, Hornets, Super Stocks, Crown Vic | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | - | - | - | - |
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| 10/27/2023 | Montpelier Motor Speedway - Montpelier, IN DIRTcar Late Models, DIRTcar UMP Modifieds, Dirt Mini Trucks, Street Stocks, Hornets, Super Stocks, Crown Vic | Results | | Jeffery Jessup (DIRTcar UMP Modifieds) | - | - | - | - |
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