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| 3/24/2019 | Cherokee Speedway - Gaffney, SC Dirt Super Late Models, Dirt Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 2nd |
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| 3/30/2019 | Fayetteville Motor Speedway - Fayetteville, NC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 3rd |
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| 4/4/2019 | Volunteer Speedway - Bulls Gap, TN Dirt Super Late Models, 604 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 5th |
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| 4/5/2019 | 411 Motor Speedway - Seymour, TN Tennessee's Action Track 50 Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds, 604 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 1st |
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| 4/6/2019 | North Georgia Speedway - Chatsworth, GA Lucas Oil Late Model Dirt Series Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds | Results | | Ross Bailes (Dirt Super Late Models) | 7th (DNF) | - | DNS | - |
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| 4/13/2019 | Smoky Mountain Speedway - Maryville, TN Smoky Mountain Spring Showdown Dirt Super Late Models, Sportsmans, Dirt Late Models, Dirt Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 2nd | - | - | 8th |
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| 4/26/2019 | Laurens County Speedway - Laurens, SC | Results | | Ross Bailes (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 | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 1st |
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| 5/17/2019 | Crossville Speedway - Crossville, TN Dirt Super Late Models, Dirt Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 5th |
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| 5/18/2019 | Thunderhill Raceway - Summertown, TN | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 1st |
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| 5/26/2019 | Rome Speedway - Rome, GA | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 8th |
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| 5/27/2019 | 411 Motor Speedway - Seymour, TN | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 9th |
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| 5/31/2019 | Cochran Motor Speedway - Cochran, GA Dirt Super Late Models: World of Outlaws - Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 4th | - | - | 8th |
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| 6/1/2019 | Lancaster Motor Speedway - Lancaster, SC Dirt Super Late Models: World of Outlaws - Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 3rd | - | - | 2nd |
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| 6/6/2019 | Eldora Speedway - Rossburg, OH Dirt Late Model Dream Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 5th | - | - | - |
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| 6/7/2019 | Eldora Speedway - Rossburg, OH Dirt Late Model Dream Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | - |
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| 6/8/2019 | Eldora Speedway - Rossburg, OH Dirt Late Model Dream Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 2nd | - | - | 13th |
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| 6/14/2019 | Cherokee Speedway - Gaffney, SC 21st Annual Grassy Smith Memorial Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 6th |
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| 6/15/2019 | Virginia Motor Speedway - Jamaica, VA USA 100 Dirt Super Late Models, Dirt Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 3rd |
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| 7/6/2019 | Lancaster Speedway - Lancaster, NY | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 1st |
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| 7/13/2019 | Wythe Raceway - Rural Retreat, VA Southern Nationals Series $10,000 to Win Dirt Lates Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | - |
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| 7/14/2019 | Cherokee Speedway - Gaffney, SC Southern Nationals Series $10,000 to Win Dirt Lates Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 4th |
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| 7/20/2019 | Screven Motor Speedway - Sylvania, GA | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 1st |
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| 7/26/2019 | 411 Motor Speedway - Seymour, TN | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 5th |
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| 7/27/2019 | Tazewell Speedway - Tazewell, TN | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 4th |
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| 8/10/2019 | Talladega Short Track - Eastaboga, AL | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 18th |
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| 8/17/2019 | Richmond Raceway (KY) - Richmond, KY | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 8th |
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| 8/30/2019 | Lavonia Speedway - Lavonia, GA | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 2nd |
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| 8/31/2019 | Lancaster Motor Speedway - Lancaster, SC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 4th |
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| 9/1/2019 | Cherokee Speedway - Gaffney, SC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 1st |
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| 9/13/2019 | Virginia Motor Speedway - Jamaica, VA FASTRAK World Championship Prelim Night DIRTcar UMP Modifieds, Dirt Crate Late Models | Results | | Ross Bailes (Dirt Crate Late Models) | 2nd | - | - | - |
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| 9/14/2019 | Virginia Motor Speedway - Jamaica, VA $50,000 To Win FASTRAK World Championship DIRTcar UMP Modifieds, Dirt Crate Late Models | Results | | Ross Bailes (Dirt Crate Late Models) | - | - | - | 2nd |
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| 9/28/2019 | Bedford Speedway - Bedford, PA | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 11th |
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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 | | Ross Bailes (Dirt Super Late Models) | 3rd | - | - | 7th |
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| 10/4/2019 | Cherokee Speedway - Gaffney, SC Dirt Super Late Models: World of Outlaws - Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 4th | - | - | 7th |
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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 | | Ross Bailes (Dirt Super Late Models) | 3rd | - | - | 20th (DNF) |
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| 10/11/2019 | Tri-County Race Track - Brasstown, NC Ray Cook's Southern National Series Dirt Late Models Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 12th |
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| 10/26/2019 | 311 Motor Speedway - Pine Hall, NC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 11th |
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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 | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 24th |
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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 | | Ross Bailes (Dirt Super Late Models) | 2nd | - | - | 28th (DNF) |
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| 11/24/2019 | Cherokee Speedway - Gaffney, SC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 2nd |
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| 12/15/2019 | Lavonia Speedway - Lavonia, GA | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 6th |
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