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| 4/20/2019 | Lake Ozark Speedway - Eldon, MO Weekly Show #1 Spring Opener USRA A-Mods & B-Mods,SS & Pure Stock,ULMA LM,LOS 360 Wing Sprints,305 Dirt Late Models: United Late Model Association 360 Sprints - Winged, 305 Sprints - Winged, Street Stocks, Pure Stock, USRA B-Mods, USRA Modifieds | Results | | Kaitlyn Boland (305 Sprints - Winged) | 4th | - | - | 5th |
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| 4/26/2019 | Lake Ozark Speedway - Eldon, MO WORLD OF OUTLAWS SPRINT CARS!!! + POWRI Racesavers, Midwest Lighting Sprints 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged, Lightning Sprints | Results | | Kaitlyn Boland (305 Sprints - Winged) | 2nd | - | - | 5th |
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| 6/8/2019 | Lake Ozark Speedway - Eldon, MO Weekly Show #6 POWRi War Sprints, 360 Sprints, POWRi Racesavers, Midwest Lighting Sprints Non-Winged Sprints: POWRi WAR Sprints 360 Sprints - Winged, 305 Sprints - Winged, 305 Sprints - Non-Winged, Lightning Sprints | Results | | Kaitlyn Boland (305 Sprints - Winged) | 3rd | - | - | 4th |
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| 6/29/2019 | Lake Ozark Speedway - Eldon, MO Weekly Show #9 360 Winged Sprints, POWRi Racesaver Sprints, USRA B-Mods, Street Stock, Pure Stock 360 Sprints - Winged, 305 Sprints - Winged, Street Stocks, Pure Stock, USRA B-Mods | Results | | Kaitlyn Boland (305 Sprints - Winged) | 4th | - | - | 5th |
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| 7/6/2019 | Lake Ozark Speedway - Eldon, MO Weekly Show #10 ASCS Warrior Sprints “Red, White & Blue Tour” $1776 to WIN!! 360 Sprints - Winged: ASCS Warrior Region 305 Sprints - Winged, Winged A-Class, Pure Stock | Results | | Kaitlyn Boland (305 Sprints - Winged) | 8th (DNF) | - | - | 7th |
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| 7/27/2019 | Lake Ozark Speedway - Eldon, MO Weekly Show #13 POWRI Racesaver Sprints $800 to WIN!! 360 Sprints - Winged, 305 Sprints - Winged, Street Stocks, Lightning Sprints, Pure Stock, USRA B-Mods | Results | | Kaitlyn Boland (305 Sprints - Winged) | 6th | - | - | 5th |
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| 8/5/2019 | Southern Iowa Speedway - Oskaloosa, IA 410 Sprints - Winged: IRA Interstate Racing Association 305 Sprints - Winged | Results | | Kaitlyn Boland (305 Sprints - Winged) | 4th | - | - | 13th |
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| 9/14/2019 | Lake Ozark Speedway - Eldon, MO Weekly Show #19 End of Season Championship Dirt Late Models: United Late Model Association 360 Sprints - Winged, 305 Sprints - Winged, Street Stocks, Pure Stock, USRA B-Mods, USRA Modifieds | Results | | Kaitlyn Boland (305 Sprints - Winged) | 6th | - | - | 6th |
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| 10/4/2019 | Lake Ozark Speedway - Eldon, MO POWRi Midwest Lighting Sprint Nationals + POWRI RaceSaver Sprints Lightning Sprints: POWRi Midwest Lightning Sprints 305 Sprints - Winged | Results | | Kaitlyn Boland (305 Sprints - Winged) | 7th | - | - | 7th |
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| 10/19/2019 | Lake Ozark Speedway - Eldon, MO Jason Johnson Classic / World Of Outlaws ! Invades For 2nd Time In 2019! 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Kaitlyn Boland (305 Sprints - Winged) | 6th | - | - | 15th (DNF) |
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