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| 2/5/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar UMP Modifieds | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 4th | - | 1st | 17th |
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| 2/6/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 5th | - | 4th | - |
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| 2/7/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 3rd | - | - | 11th |
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| 2/8/2019 | Volusia Speedway Park - De Leon Springs, FL DirtCar Nationals 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | - | - | - | - |
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| 2/9/2019 | Volusia Speedway Park - De Leon Springs, FL DirtCar Nationals 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 10th (DNF) | - | 4th | - |
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| 2/11/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | - | - | 3rd | 24th |
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| 4/5/2019 | Farmer City Raceway - Farmer City, IL Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Ray Bollinger (A Modifieds) | 5th | - | - | - |
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| 4/6/2019 | Farmer City Raceway - Farmer City, IL Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Ray Bollinger (A Modifieds) | 5th | - | - | 7th |
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| 4/12/2019 | Lincoln Speedway - Lincoln, IL Railsplitter 40 Street Stocks: Midwest Stock Car Tour Economy Midgets, DIRTcar UMP Modifieds, Hornets, Pro Late Model | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 2nd | - | - | 2nd |
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| 4/13/2019 | Peoria Speedway - Peoria, IL Chuck Hamilton Memorial DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks, Hornets | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 3rd | - | - | 6th |
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| 4/26/2019 | Lincoln Speedway - Lincoln, IL Fan Appreciation Night / $10 Admission Night / $1 Hot Dogs & $2 Beers 305 Sprints - Winged, Economy Midgets, DIRTcar UMP Modifieds, Hornets, Pro Late Model | Results | | Ray Bollinger (Economy Midgets) | 4th | - | - | 13th (DNF) | | Ray Bollinger (DIRTcar UMP Modifieds) | 1st | - | - | 17th (DNF) |
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| 5/3/2019 | Lincoln Speedway - Lincoln, IL Ladies Night / $5.00 Ladies Admission in Grandstands Economy Midgets, DIRTcar UMP Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 1st | - | - | 1st |
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| 5/24/2019 | Farmer City Raceway - Farmer City, IL A Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Ray Bollinger (A Modifieds) | 7th | - | 2nd | 5th |
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| 5/25/2019 | Fairbury Speedway - Fairbury, IL Memorial Day Weekend Roundup DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks, Pro Late Model | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 3rd | - | - | 7th |
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| 5/27/2019 | Macon Speedway - Macon, IL Mueller Dist. Miller Lite Twin 50s (Super Late Models and Pro Mods) & City of Macon Night DIRTcar Late Models, DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 4th | - | - | 4th |
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| 5/27/2019 | Peoria Speedway - Peoria, IL Joe Wagner Memorial DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks, Hornets | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | - | - | - | - |
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| 6/4/2019 | Fairbury Speedway - Fairbury, IL 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 2nd | - | - | 2nd |
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| 6/7/2019 | Lincoln Speedway - Lincoln, IL 4th Hornet Challenge $1,000 to Win Economy Midgets, DIRTcar UMP Modifieds, B Modifieds, Hornets, Pro Late Model | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 1st | - | - | 1st |
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| 6/13/2019 | Kankakee County Speedway - Kankakee, IL DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 1st | - | - | 10th |
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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 | | Ray Bollinger (DIRTcar UMP Modifieds) | 1st | - | - | 3rd |
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| 6/20/2019 | Spoon River Speedway - Canton, IL DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 3rd | - | - | 15th (DNF) |
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| 6/22/2019 | Fairbury Speedway - Fairbury, IL UMP Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models, DIRTcar Sportsmans | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 3rd | - | - | 14th |
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| 6/25/2019 | Tri City Speedway - Granite City, IL "Summer Nationals" MAKEUP from 6/21st UMP LM $7,500/UMP Summit Mods $1000/B-Mods $1000 DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models, B Modifieds | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 5th | - | 4th | 15th (DNF) |
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| 6/26/2019 | Peoria Speedway - Peoria, IL Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models, B Modifieds, Hornets | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 3rd | - | - | 20th (DNF) |
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| 7/4/2019 | Macon Speedway - Macon, IL Herald & Review 100 Featuring the Summernationals Hell Tour DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals B Modifieds | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | - | - | - | 8th |
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| 7/5/2019 | Farmer City Raceway - Farmer City, IL DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models, A Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Ray Bollinger (A Modifieds) | 1st | - | - | 5th |
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| 7/12/2019 | Lincoln Speedway - Lincoln, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Economy Midgets, DIRTcar UMP Modifieds, 600cc Modifieds, Pro Late Model | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 3rd | - | - | 11th (DNF) |
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| 7/21/2019 | Lincoln Speedway - Lincoln, IL Central Illinois Motorsports Nostalgia Reunion ( Featuring Springfield & Macon Speedways) 305 Sprints - Winged, Economy Midgets, DIRTcar UMP Modifieds, Street Stocks, Hornets, Pro Late Model | Rain Out |
| 7/26/2019 | Fairbury Speedway - Fairbury, IL WORLD OF OUTLAWS PDC SHOWDOWN Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: DIRTcar Modified Nationals DIRTcar Late Models | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | - | - | - | 6th |
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| 7/27/2019 | Fairbury Speedway - Fairbury, IL 30TH ANNUAL WoO PRAIRIE DIRT CLASSIC Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: DIRTcar Modified Nationals DIRTcar Late Models | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | - | - | 4th | 13th |
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| 8/9/2019 | Lincoln Speedway - Lincoln, IL All American Night of Speed 305 Sprints - Winged, Economy Midgets, DIRTcar UMP Modifieds, B Modifieds, Hornets, Pro Late Model | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 2nd | - | - | 1st |
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| 8/16/2019 | Tri City Speedway - Granite City, IL "Russ Wallace Memorial-Topless Night" MARS Late Models $3,000/UMP Modifieds/B-Modifieds/UMP Crate LM DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Pro Late Model | Results | | Ray Bollinger (DIRTcar UMP Modifieds) | 5th | - | - | 17th |
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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 | | Ray Bollinger (A Modifieds) | 8th | - | 4th | 11th |
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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 | | Ray Bollinger (A Modifieds) | - | - | 6th (DNF) | 17th (DNF) |
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