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| 1/26/2020 | Cherokee Speedway - Gaffney, SC Drydene Xtreme DIRTcar Series Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 1st |
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| 1/30/2020 | Golden Isles Speedway - Waynesville, GA Super Bowl of Racing Practice Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | - |
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| 1/31/2020 | Golden Isles Speedway - Waynesville, GA Rhino Ag Super Bowl of Racing - Presented by General Tire Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Rain Out |
| 2/1/2020 | Golden Isles Speedway - Waynesville, GA RhinoAg Super Bowl 2020 Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | 4th | - | - | 25th |
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| 2/7/2020 | Screven Motor Speedway - Sylvania, GA Winter Freeze X A Modifieds: Southeastern Modified Series Hobby Stocks, Dirt Late Models, Pony Stock, Dirt Crate Late Models | Results | | Ross Bailes (Dirt Late Models) | 1st | - | - | 2nd |
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| 2/8/2020 | Screven Motor Speedway - Sylvania, GA Winter Freeze X A Modifieds: Southeastern Modified Series Hobby Stocks, Dirt Late Models, Pony Stock, Dirt Crate Late Models | Results | | Ross Bailes (Dirt Late Models) | 2nd | - | - | 2nd |
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| 2/29/2020 | Modoc Raceway - Modoc, SC Xtreme Dirtcar Series Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 3rd | - | - | 8th |
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| 3/1/2020 | Cherokee Speedway - Gaffney, SC March Madness Day 2 Dirt Super Late Models, CRUSA Dirt Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 4th | - | - | 8th |
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| 3/7/2020 | Lancaster Motor Speedway - Lancaster, SC Red Rose Rumble Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | DNS |
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| 5/1/2020 | Lancaster Motor Speedway - Lancaster, SC Lancaster Lidlifter presented by PitStopUSA.com Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 2nd |
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| 5/2/2020 | Cherokee Speedway - Gaffney, SC Palmetto Invitational Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 4th | - | - | 7th |
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| 5/7/2020 | Senoia Raceway - Senoia, GA DirtonDirt.com Shootout Dirt Super Late Models, Dirt Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 6th |
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| 5/18/2020 | Golden Isles Speedway - Waynesville, GA Practice Golden Isles Speedway Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | - |
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| 5/19/2020 | Golden Isles Speedway - Waynesville, GA The OPTIMA Batteries Golden Isles Nationals Presented By Bilstein Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | 8th | - | 5th | - |
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| 5/20/2020 | Golden Isles Speedway - Waynesville, GA The OPTIMA Batteries Golden Isles Nationals Presented By Bilstein Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | 9th | - | DNS | - |
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| 5/21/2020 | Golden Isles Speedway - Waynesville, GA The OPTIMA Batteries Golden Isles Nationals Presented By Bilstein Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | 5th | - | 2nd | 18th |
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| 6/12/2020 | Cherokee Speedway - Gaffney, SC 22nd Annual Grassy Smith Memorial Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 1st |
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| 6/13/2020 | Ultimate Motorsports & RV Park - Elkin, NC ULTIMATE SUPER LATE MODELS! A Modifieds, Street Stocks, Hornets, Pony Stock, Pure Stock, Dirt Crate Late Models, USRA Late Models | Results | | Ross Bailes (USRA Late Models) | - | - | - | - |
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| 6/18/2020 | Magnolia Motor Speedway - Columbus, MS Clash at the Mag Dirt Super Late Models: Lucas Oil Late Model Dirt Series with COMP Cams Super Dirt Series (CCSDS) | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 3rd |
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| 6/19/2020 | Magnolia Motor Speedway - Columbus, MS Clash at the Mag Dirt Super Late Models: Lucas Oil Late Model Dirt Series with COMP Cams Super Dirt Series (CCSDS) Dirt Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 6th | - | 10th | - |
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| 6/20/2020 | Magnolia Motor Speedway - Columbus, MS Clash at the Mag Dirt Super Late Models: Lucas Oil Late Model Dirt Series with COMP Cams Super Dirt Series (CCSDS) | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 16th |
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| 7/3/2020 | Lavonia Speedway - Lavonia, GA | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 2nd |
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| 7/4/2020 | Cherokee Speedway - Gaffney, SC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 2nd |
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| 7/10/2020 | Smoky Mountain Speedway - Maryville, TN Smoky Mountain Summer Showdown Dirt Super Late Models, Sportsmans, Dirt Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 5th |
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| 7/11/2020 | Wythe Raceway - Rural Retreat, VA | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 4th |
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| 7/13/2020 | Volunteer Speedway - Bulls Gap, TN | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 4th |
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| 7/14/2020 | I-75 Raceway - Sweetwater, TN | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 12th |
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| 7/16/2020 | Senoia Raceway - Senoia, GA Schaeffer's Oil Southern Nationals Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 11th |
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| 7/17/2020 | Needmore Speedway - Norman Park, GA Dirt Super Late Models, Dirt Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 6th |
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| 7/18/2020 | Screven Motor Speedway - Sylvania, GA | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 3rd |
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| 7/19/2020 | Cochran Motor Speedway - Cochran, GA | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 3rd |
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| 7/21/2020 | Tri-County Race Track - Brasstown, NC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 8th |
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| 7/23/2020 | Crossville Speedway - Crossville, TN | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 6th |
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| 7/24/2020 | 411 Motor Speedway - Seymour, TN Schaeffer’s Oil Southern Nationals Super Late Models Dirt Super Late Models, Sportsmans, A Modifieds, Dirt Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 5th |
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| 7/25/2020 | Tazewell Speedway - Tazewell, TN | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 12th |
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| 8/1/2020 | Cherokee Speedway - Gaffney, SC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 1st |
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| 8/6/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models USRA Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 2nd | - | - | 8th |
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| 8/7/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds, Dirt Late Models, USRA Modifieds | Results | | Ross Bailes (Dirt Super Late Models) | 9th | 3rd | - | - |
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| 8/8/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models, USRA Modifieds | Results | | Ross Bailes (Dirt Super Late Models) | - | - | 5th | 10th |
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| 8/12/2020 | Florence Speedway - Walton, KY Ralph Latham Memorial Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds | Results | | Ross Bailes (Dirt Super Late Models) | 7th | - | 10th | - |
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| 8/13/2020 | Florence Speedway - Walton, KY Sunoco North/South Shootout Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds | Results | | Ross Bailes (Dirt Super Late Models) | 5th | - | 4th | - |
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| 8/15/2020 | Florence Speedway - Walton, KY 38th Annual Sunoco North/South 100 Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds | Results | | Ross Bailes (Dirt Super Late Models) | 3rd | - | - | 17th |
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| 9/4/2020 | Lavonia Speedway - Lavonia, GA | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 7th |
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| 9/5/2020 | Lancaster Motor Speedway - Lancaster, SC World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 3rd |
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| 9/6/2020 | Cherokee Speedway - Gaffney, SC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 3rd |
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| 9/10/2020 | Eldora Speedway - Rossburg, OH 2020 Intercontinental Classic Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | 9th | - |
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| 9/11/2020 | Eldora Speedway - Rossburg, OH 2020 Intercontinental Classic Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 20th (DNF) |
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| 9/12/2020 | Eldora Speedway - Rossburg, OH 2020 Intercontinental Classic Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 8th | - | DNS | - |
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| 9/15/2020 | Laurens County Speedway - Laurens, SC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 1st |
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| 9/19/2020 | Richmond Raceway (KY) - Richmond, KY | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 4th |
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| 10/2/2020 | Cherokee Speedway - Gaffney, SC World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 5th |
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| 10/3/2020 | 411 Motor Speedway - Seymour, TN World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models Sportsmans, A Modifieds, Street Stocks, Vintage Modifieds, Dirt Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 5th |
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| 10/16/2020 | Portsmouth Raceway Park - Portsmouth, OH 40th Annual Dirt Track World Championship Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds: Renegades of Dirt Modified Tour Pro Legends, Economy Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 6th | - | - | - |
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| 10/17/2020 | Portsmouth Raceway Park - Portsmouth, OH 40th Annual Dirt Track World Championship Dirt Super Late Models: Lucas Oil Late Model Dirt Series Economy Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | DNS | - |
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| 10/17/2020 | Sumter Speedway - Sumter, SC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 1st |
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| 10/23/2020 | All-Tech Raceway - Lake City, FL 25th Annual Powell Memorial CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Economy Late Models, Pure Stock | Results | | Ross Bailes (Dirt Late Models) | 11th | - | 4th | 18th |
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| 11/4/2020 | The Dirt Track at Charlotte - Concord, NC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 24th |
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| 11/5/2020 | The Dirt Track at Charlotte - Concord, NC Can-Am World Finals Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 21st |
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| 11/6/2020 | Lancaster Motor Speedway - Lancaster, SC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 1st |
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| 11/7/2020 | Carolina Speedway - Gastonia, NC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 1st |
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| 11/14/2020 | Modoc Raceway - Modoc, SC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 12th |
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| 11/21/2020 | Lancaster Motor Speedway - Lancaster, SC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 3rd |
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| 11/22/2020 | Cherokee Speedway - Gaffney, SC | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 6th |
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