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| 5/17/2019 | Belle-Clair Speedway - Belleville, IL Southern Illinois Shootout DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged Outlaw, B Modifieds | Results | | Matt Bailey (DIRTcar Late Models) | 4th | - | - | 5th |
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| 5/18/2019 | Highland Speedway - Highland, IL Big 10 race DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Matt Bailey (DIRTcar Late Models) | 2nd | 3rd | - | 3rd |
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| 5/25/2019 | Highland Speedway - Highland, IL Race night DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Matt Bailey (DIRTcar Late Models) | 3rd | - | - | 5th |
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| 5/31/2019 | Belle-Clair Speedway - Belleville, IL Lucas OIl MLRA Late Models Dirt Super Late Models: Lucas Oil MLRA DIRTcar Late Models, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged Outlaw, B Modifieds | Results | | Matt Bailey (Dirt Super Late Models) | 2nd | - | - | 7th |
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| 6/1/2019 | Highland Speedway - Highland, IL Race night DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Matt Bailey (DIRTcar Late Models) | 2nd | 4th | - | 2nd |
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| 6/18/2019 | Jacksonville Speedway - Jacksonville, IL DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models | Results | | Matt Bailey (DIRTcar Late Models) | 6th | - | 1st | 22nd (DNF) |
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| 7/13/2019 | Highland Speedway - Highland, IL "Mr. Joe" Schmitt Memorial race DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Matt Bailey (DIRTcar Late Models) | 1st | 1st | - | 4th |
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| 7/27/2019 | Highland Speedway - Highland, IL Scott Wernle & Kyle Roberts Annual Memorial Race DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Matt Bailey (DIRTcar Late Models) | 1st | 2nd | - | 3rd |
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| 8/2/2019 | Belle-Clair Speedway - Belleville, IL The Talker Guy 100 DIRTcar Late Models, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged A-Class, B Modifieds | Results | | Matt Bailey (DIRTcar Late Models) | 4th | - | - | 8th |
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| 8/3/2019 | Highland Speedway - Highland, IL Leaps of Love DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Matt Bailey (DIRTcar Late Models) | 2nd | 3rd | - | 1st |
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| 8/10/2019 | Highland Speedway - Highland, IL Big 10 race DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Matt Bailey (DIRTcar Late Models) | 2nd | 4th | - | 1st |
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| 8/23/2019 | Belle-Clair Speedway - Belleville, IL Big Ten Series DIRTcar Late Models, DIRTcar UMP Modifieds, Winged A-Class, B Modifieds | Results | | Matt Bailey (DIRTcar Late Models) | 4th | - | - | 7th |
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| 9/13/2019 | Tri City Speedway - Granite City, IL "Fan Appreciation Night" UMP LM/UMP Mods/B-Mods/UMP Crate LM/UMP St. Stocks/Non-Wing Micros DIRTcar Late Models, DIRTcar UMP Modifieds, Non-Wing Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Matt Bailey (DIRTcar Late Models) | 4th | - | - | 7th |
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| 9/20/2019 | Tri City Speedway - Granite City, IL Season Championship - UMP Late Models/UMP Modifieds/B-Modifieds/UMP Crate LM/UMP St. Stocks/Micros DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Matt Bailey (DIRTcar Late Models) | 2nd | - | - | 5th |
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| 9/21/2019 | Federated Auto Parts I-55 Raceway - Pevely, MO Pepsi Nationals DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, DIRTcar Sport Compact, B Modifieds | Results | | Matt Bailey (DIRTcar Late Models) | 4th | - | - | 11th |
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| 10/25/2019 | Quincy Raceways - Quincy, IL Kenny Pratt Memorial Friday Night Stock Cars, Dirt Late Models, Dirt Crate Late Models | Results | | Matt Bailey (Dirt Late Models) | 2nd | - | - | 7th |
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| 10/27/2019 | Quincy Raceways - Quincy, IL Kenny Pratt Postponed 2nd night Stock Cars, Dirt Late Models, Dirt Crate Late Models | Results | | Matt Bailey (Dirt Late Models) | 3rd | - | - | 5th |
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| 11/24/2019 | Springfield Raceway - Springfield, MO TURKEY BOWL XIII A Modifieds, Midwest Modifieds, Dirt Late Models, Pro Legends, USRA B-Mods, Dirt Mini Late Models | Results | | Matt Bailey (Dirt Late Models) | 5th | - | DNS | - |
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