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| 1/5/2019 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Round 1 Dirt Super Late Models, A Modifieds, B Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 5th | - | 1st | 4th |
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| 1/6/2019 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Round 2 Dirt Super Late Models, A Modifieds, B Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 8th |
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| 1/9/2019 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Round 3 Dirt Super Late Models, A Modifieds, B Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 4th |
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| 1/11/2019 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Round 4 Dirt Super Late Models, A Modifieds, B Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 4th | - | - | 11th |
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| 1/12/2019 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Round 5 Dirt Super Late Models, A Modifieds, B Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 1/13/2019 | Arizona Speedway - Queen Creek, AZ Wild West Shootout Round 6 Dirt Super Late Models, A Modifieds, B Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 9th |
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| 2/8/2019 | Screven Motor Speedway - Sylvania, GA Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 8th | - | 7th | 14th |
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| 2/9/2019 | Screven Motor Speedway - Sylvania, GA Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 19th |
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| 2/11/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Cade Dillard (DIRTcar Late Models) | 3rd | - | - | 16th |
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| 2/13/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series Dirt Big Block Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 9th | - | 9th | - |
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| 2/14/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 6th | - | 6th | - |
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| 2/15/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 13th |
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| 2/16/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 7th | - | 7th | - |
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| 3/22/2019 | Duck River Raceway Park - Shelbyville, TN World of Outlaws 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models Hobby Stocks, Sportsmans, B Modifieds, Street Stocks, Pony Stock, Dirt Crate Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 7th (DNF) | - | 2nd | 16th |
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| 3/23/2019 | Smoky Mountain Speedway - Maryville, TN Tennessee Tipoff Classic Dirt Super Late Models: World of Outlaws - Late Models Hornets, Dirt Crate Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 5th | - | 3rd | 15th |
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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 | | Cade Dillard (Dirt Super Late Models) | 7th | - | 2nd | 15th |
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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 | | Cade Dillard (Dirt Super Late Models) | 4th | - | - | 24th (DNF) |
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| 4/11/2019 | Ark-La-Tex Speedway - Vivian, LA 7th Annual Cajun Clash A Modifieds: USMTS - United States Modified Touring Series USRA Limited Mods, USRA Factory Stocks | Results | | Cade Dillard (A Modifieds) | 1st | - | - | 2nd |
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| 4/12/2019 | Ark-La-Tex Speedway - Vivian, LA 7th Annual Cajun Clash A Modifieds: USMTS - United States Modified Touring Series USRA Limited Mods, USRA Factory Stocks | Results | | Cade Dillard (A Modifieds) | 1st | - | - | 2nd |
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| 4/26/2019 | Sabine Speedway - Many, LA | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 1st |
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| 5/3/2019 | Cherokee Speedway - Gaffney, SC Dirt Super Late Models: World of Outlaws - Late Models A Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 10th (DNF) | - | 6th | 17th |
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| 5/18/2019 | Wayne County Speedway - Orrville, OH Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 6th |
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| 5/25/2019 | Thunder Valley Speedway (LA) - Glenmora, LA | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 16th (DNF) |
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| 5/30/2019 | Magnolia Motor Speedway - Columbus, MS Clash at the Mag Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds, Street Stocks | Results | | Cade Dillard (Dirt Super Late Models) | 4th | - | - | 13th |
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| 5/31/2019 | Cochran Motor Speedway - Cochran, GA Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 7th | - | - | 11th |
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| 6/1/2019 | Lancaster Motor Speedway - Lancaster, SC Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 17th (DNF) |
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| 6/4/2019 | Hunt County Raceway - Greenville, TX USMTS A Modifieds: USMTS - United States Modified Touring Series USRA Limited Mods, USRA Factory Stocks | Results | | Cade Dillard (A Modifieds) | 1st | - | - | 4th |
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| 6/21/2019 | Lernerville Speedway - Sarver, PA Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 5th | - | 2nd | 18th |
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| 6/22/2019 | Lernerville Speedway - Sarver, PA Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series | Results | | Cade Dillard (Dirt Super Late Models) | 9th | - | 13th (DNF) | 22nd |
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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 | | Cade Dillard (DIRTcar Late Models) | 5th | - | 2nd | 21st (DNF) |
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| 6/27/2019 | Brownstown Speedway - Brownstown, IN DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models | Results | | Cade Dillard (DIRTcar Late Models) | 1st | - | - | 7th |
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| 6/28/2019 | Terre Haute Action Track - Terre Haute, IN World Of Outlaw LM vs. Summer National LM Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Cade Dillard (Dirt Super Late Models) | 5th | - | - | 12th |
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| 7/5/2019 | Independence Motor Speedway - Independence, IA Dirt Super Late Models: World of Outlaws - Late Models Stock Cars, A Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 4th | - | - | 10th |
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| 7/6/2019 | Deer Creek Speedway - Spring Valley, MN Bigelow Homes Gopher 50 Dirt Super Late Models: World of Outlaws - Late Models USRA Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 6th | - | - | 13th |
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| 7/7/2019 | Eagle Valley Speedway - Jim Falls, WI Credit King Auto Sales Independence Day Bash - Dirt Kings Late Model Series - Fireworks Special Dirt Late Models: Dirt Kings Late Model Tour Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cade Dillard (Dirt Late Models) | 1st | - | - | 1st |
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| 7/9/2019 | ABC Raceway - Ashland, WI Red's Auto Badgerland 50 World of Outlaws Craftsman Late Model Series Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models, Dirt 6-cyl Stock Cars, WISSOTA Midwest Mods, WISSOTA Super Stock | Results | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 5th |
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| 7/12/2019 | River Cities Speedway - Grand Forks, ND World Of Outlaws Late Models, NOSA Sprints, & A-Mods 410 Sprints - Winged: Northern Outlaw Sprint Association Dirt Super Late Models: World of Outlaws - Late Models B Modifieds, Dirt Late Models, WISSOTA Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 17th (DNF) |
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| 7/13/2019 | Ogilvie Raceway - Ogilvie, MN World Of Outlaw Late Models & Fastlane Super Stock Special Dirt Super Late Models: World of Outlaws - Late Models WISSOTA Super Stock: Fast Lane Motorsports Northland Super Stock Series | Results | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 9th |
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| 7/14/2019 | Red Cedar Speedway - Menomonie, WI Rumble At The Red Cedar World Of Outlaw Late Models Dirt Super Late Models: World of Outlaws - Late Models WISSOTA Midwest Mods | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | - |
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| 7/24/2019 | Davenport Speedway - Davenport, IA World Of Outlaws Morton Buildings Late Model Series Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, B Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 3rd |
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| 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 | | Cade Dillard (DIRTcar Late Models) | - | - | - | 14th (DNF) |
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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 | | Cade Dillard (DIRTcar Late Models) | - | - | 15th (DNF) | 12th |
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| 7/29/2019 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI Dirt Super Late Models: World of Outlaws - Late Models B Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 6th |
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| 7/30/2019 | Shawano Speedway - Shawano, WI World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models Stock Cars, A Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 6th |
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| 8/1/2019 | Cedar Lake Speedway - New Richmond, WI Dirt Super Late Models: World of Outlaws - Late Models USRA Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 4th | - | - | 16th |
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| 8/2/2019 | Cedar Lake Speedway - New Richmond, WI Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 2nd | 2nd | - | - |
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| 8/3/2019 | Cedar Lake Speedway - New Richmond, WI Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Cade Dillard (Dirt Super Late Models) | - | - | - | 13th |
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| 8/16/2019 | Williams Grove Speedway - Mechanicsburg, PA Dirt Super Late Models: World of Outlaws - Late Models 410 Sprints - Winged | Results | | Cade Dillard (Dirt Super Late Models) | 5th | - | - | 10th |
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| 8/17/2019 | Port Royal Speedway - Port Royal, PA Dirt Super Late Models: World of Outlaws - Late Models 410 Sprints - Winged | Results | | Cade Dillard (Dirt Super Late Models) | 4th | - | - | 13th |
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| 8/29/2019 | I-96 Speedway - Lake Odessa, MI World of Outlaws Craftsman Late Model Series & American Ethanol Modified Tour Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 5th |
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| 8/30/2019 | Sharon Speedway - Hartford, OH Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 8th |
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| 9/13/2019 | Texas Motor Speedway - Fort Worth, TX Southern Dirt Nationals 305 Sprints - Winged: IMCA RaceSaver Sprints Factory Stocks, A Modifieds, B Modifieds, Dirt Late Models | Results | | Cade Dillard (A Modifieds) | 1st | - | - | - | | Cade Dillard (Dirt Late Models) | 1st | - | - | 1st |
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| 9/14/2019 | Texas Motor Speedway - Fort Worth, TX Southern Dirt Nationals 305 Sprints - Winged: IMCA RaceSaver Sprints Factory Stocks, A Modifieds, B Modifieds, Dirt Late Models | Results | | Cade Dillard (A Modifieds) | - | - | - | 1st | | Cade Dillard (Dirt Late Models) | 1st | - | - | 2nd |
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| 9/19/2019 | Stateline Speedway - Busti, NY Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 6th |
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| 9/20/2019 | Outlaw Speedway - Dundee, NY 360 Sprints - Winged: PST-Patriot Sprint Tour Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 1st | - | - | 4th |
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| 9/21/2019 | Selinsgrove Speedway - Selinsgrove, PA Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 3rd | - | - | 9th |
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| 10/3/2019 | Lavonia Speedway - Lavonia, GA Dirt Super Late Models: World of Outlaws - Late Models Dirt Crate Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 6th | - | - | 18th (DNF) |
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| 10/4/2019 | Cherokee Speedway - Gaffney, SC Dirt Super Late Models: World of Outlaws - Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 7th | - | 2nd | 10th |
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| 10/5/2019 | 411 Motor Speedway - Seymour, TN Dirt Super Late Models: World of Outlaws - Late Models 604 Crate Late Models | Results | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 4th |
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| 10/25/2019 | Vado Speedway Park - Vado, NM 20th Annual Toyota USRA Fall Nationals Dirt Super Late Models, A Modifieds, USRA B-Mods, USRA Modifieds, USRA Stock Cars | Results | | Cade Dillard (USRA Modifieds) | 2nd | - | - | 1st |
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| 10/27/2019 | Vado Speedway Park - Vado, NM 20th Annual Toyota USRA Fall Nationals Dirt Super Late Models, A Modifieds, USRA B-Mods, USRA Modifieds, USRA Stock Cars | Results | | Cade Dillard (USRA Modifieds) | - | - | - | 1st |
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| 11/8/2019 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 2nd | - | - | 5th |
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| 11/9/2019 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Cade Dillard (Dirt Super Late Models) | 5th | - | 15th (DNF) | 29th (DNF) |
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