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| 1/18/2023 | Volusia Speedway Park - De Leon Springs, FL 4th Annual DIRTcar Sunshine Nationals - Practice Dirt Super Late Models: World of Outlaws - Late Models Dirt Crate Late Models, 604 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | - | | Ross Bailes (604 Crate Late Models) | - | - | - | - |
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| 1/19/2023 | Volusia Speedway Park - De Leon Springs, FL 4th Annual DIRTcar Sunshine Nationals - Night #1 Dirt Super Late Models: World of Outlaws - Late Models Dirt Crate Late Models, 604 Crate Late Models | Results | | Ross Bailes (604 Crate Late Models) | - | - | - | 17th |
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| 1/20/2023 | Volusia Speedway Park - De Leon Springs, FL 4th Annual DIRTcar Sunshine Nationals - Night #2 Dirt Super Late Models: World of Outlaws - Late Models Dirt Crate Late Models, 604 Crate Late Models | Results | | Ross Bailes (604 Crate Late Models) | - | - | - | 2nd |
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| 1/21/2023 | Volusia Speedway Park - De Leon Springs, FL 4th Annual DIRTcar Sunshine Nationals - Night #3 Dirt Super Late Models: World of Outlaws - Late Models Dirt Crate Late Models, 604 Crate Late Models | Rain Out |
| 2/4/2023 | Screven Motor Speedway - Sylvania, GA Winter Freeze XIII Day 2 Dirt Super Late Models: Southern All Stars Sport Compact: SCDRA - Sport Compact Dirt Racing Association Stock Cars, Street Stocks, Dirt Mini Late Models, CRUSA Modified Sportsman, Crown Vic, 602 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 1st |
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| 2/5/2023 | East Bay Raceway Park - Tampa, FL 47th Annual Wieland Winternationals - PRACTICE Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | - |
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| 2/6/2023 | East Bay Raceway Park - Tampa, FL 47th Annual Wieland Winternationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | 2nd | - | - | 12th |
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| 2/7/2023 | East Bay Raceway Park - Tampa, FL 47th Annual Wieland Winternationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | 3rd | - | - | 19th |
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| 2/8/2023 | East Bay Raceway Park - Tampa, FL 47th Annual Wieland Winternationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | 2nd | - | - | 25th |
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| 2/9/2023 | East Bay Raceway Park - Tampa, FL 47th Annual Wieland Winternationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | 2nd | - | - | 26th |
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| 2/10/2023 | East Bay Raceway Park - Tampa, FL 47th Annual Wieland Winternationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Ross Bailes (Dirt Super Late Models) | 4th | - | 2nd | 20th |
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| 3/3/2023 | Swainsboro Raceway - Swainsboro, GA Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 9th |
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| 3/4/2023 | Senoia Raceway - Senoia, GA Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals Hobby Stocks, Sportsmans, Street Stocks, Dirt Late Models, Pony Stock, Dirt Crate Late Models, Asphalt Bombers | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 2nd |
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| 3/5/2023 | Cherokee Speedway - Gaffney, SC March Madness Day#2 SAS SLM $20,000/$1,000 Dirt Super Late Models: Southern All Stars Street Stocks: Mid-East Racing Association Factory Stocks, Stock Cars, 604 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 5th | - | - | 11th |
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| 3/10/2023 | North Georgia Speedway - Chatsworth, GA Biddle Ridley Memorial Dirt Super Late Models: Schaeffer's Oil Southern Nationals | Rain Out |
| 3/11/2023 | 411 Motor Speedway - Seymour, TN The Tennessean Dirt Super Late Models: Schaeffer's Oil Southern Nationals Sportsmans, Vintage Modifieds, Economy Late Models, Asphalt Mini Stock, Dirt Crate Late Models, Crown Vic, 602 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 10th |
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| 3/24/2023 | Volunteer Speedway - Bulls Gap, TN XR Super Series $5,000-to-WIN x2 Dirt Super Late Models: Iron-Man Late Model Series with XR Super Series A Modifieds: Iron-Man Modified Series | Rain Out |
| 3/25/2023 | Volunteer Speedway - Bulls Gap, TN XR Super Series $100,000-to-WIN Dirt Super Late Models: Iron-Man Late Model Series with XR Super Series A Modifieds: Iron-Man Modified Series | Rain Out |
| 3/31/2023 | Buckshot Speedway - Clanton, AL Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals CRUSA Dirt Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 3rd |
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| 4/1/2023 | East Alabama Motor Speedway - Phenix City, AL Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals Factory Stocks, Hobby Stocks, Enduro, Dirt Crate Late Models, 602 Crate Late Models, 604 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 3rd | - | - | 15th |
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| 4/6/2023 | Volunteer Speedway - Bulls Gap, TN Dirt Super Late Models, Economy Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 4th | - | - | 11th |
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| 4/7/2023 | Wythe Raceway - Rural Retreat, VA Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals Street Stocks, Hornets, Limited Modified, Sport Compact, Dirt Mini Stocks | Rain Out |
| 4/8/2023 | Tazewell Speedway - Tazewell, TN Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals with Iron-Man Late Model Series | Postponed |
| 4/13/2023 | Volunteer Speedway - Bulls Gap, TN XR Super Series Practice Dirt Super Late Models: XR Super Series | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | - |
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| 4/14/2023 | Volunteer Speedway - Bulls Gap, TN XR Super Series $5,000-to-WIN x2 Dirt Super Late Models: XR Super Series A Modifieds, Economy Late Models | Rain Out |
| 4/15/2023 | Volunteer Speedway - Bulls Gap, TN XR Super Series $100,000-to-WIN Dirt Super Late Models: XR Super Series A Modifieds, Economy Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 10th (DNF) | - | DNS | - |
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| 4/21/2023 | Lavonia Speedway - Lavonia, GA The Buck Simmons Memorial Dirt Super Late Models: Carolina Clash Super Late Model Series Stock Cars, Hornets, Economy Late Models, Super Stocks, Dirt Mini Stocks, 602 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 16th |
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| 4/22/2023 | Cherokee Speedway - Gaffney, SC Stick Elliott Memorial (Carolina Clash SLM) ($5,000) Dirt Super Late Models: Carolina Clash Super Late Model Series Factory Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Pure Stock, 604 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 4th |
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| 4/27/2023 | Crossville Speedway - Crossville, TN Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals | Rain Out |
| 4/28/2023 | Lake Cumberland Speedway - Somerset, KY Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals | Rain Out |
| 4/29/2023 | Clarksville Speedway - Clarksville, TN Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals | Rain Out |
| 5/5/2023 | Tri-County Race Track - Brasstown, NC Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 7th |
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| 5/6/2023 | Rome Speedway - Rome, GA Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals Stock Cars, B Modifieds, Hornets, Dirt Limited Late Models, 602 Crate Late Models, 604 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 3rd | - | - | 5th |
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| 5/19/2023 | Beckley Motor Speedway - Mount Hope, WV 13th Annual UBB Miners Memorial Pro Late Model: American All-Star Series A Modifieds, Street Stocks, Dirt Late Models, Enduro, Mini Wedge | Results | | Ross Bailes (Pro Late Model) | 1st | - | - | - |
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| 5/20/2023 | Beckley Motor Speedway - Mount Hope, WV 13th Annual UBB Miners Memorial Pro Late Model: American All-Star Series B Modifieds, Hornets, Mini Wedge, Kid Karts Dirt, Outlaw Hobby Stocks | Postponed |
| 5/21/2023 | Beckley Motor Speedway - Mount Hope, WV 13th Annual UBB Miners Memorial Race B Modifieds, Dirt Late Models, Hornets, Pro Late Model, Mini Wedge, Kid Karts Dirt, Outlaw Hobby Stocks | Results | | Ross Bailes (Pro Late Model) | - | - | - | 17th |
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| 5/25/2023 | Cherokee Speedway - Gaffney, SC Throwback 50 - XR Workin' Man Super Late Models Dirt Super Late Models: XR Workin' Man Series Factory Stocks, Hornets | Results | | Ross Bailes (Dirt Super Late Models) | 2nd | - | - | 1st |
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| 5/26/2023 | I-75 Raceway - Sweetwater, TN Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals Factory Stocks, Asphalt Mini Stocks, Super Sports, Asphalt 4-Cylinders, Asphalt Rookie Stocks | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 2nd |
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| 5/27/2023 | North Georgia Speedway - Chatsworth, GA Dirt Super Late Models: Schaeffer's Oil Southern Nationals Hornets, Economy Late Models, 602 Crate Late Models, 604 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 2nd | - | - | 2nd |
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| 5/28/2023 | Duck River Raceway Park - Shelbyville, TN Schaeffer's Oil Spring Nationals Dirt Super Late Models: Schaeffer's Oil Southern Nationals Young Guns, Dwarf, Hornets, Pony Stock, Dirt 4 cyl Modifieds, Pure Stock, CRUSA Modified Sportsman, 602 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 4th | - | - | 14th |
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| 6/8/2023 | Eldora Speedway - Rossburg, OH DLM Dream XXIX Dirt Super Late Models, DIRTcar Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 7th | - | 3rd | - |
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| 6/9/2023 | Eldora Speedway - Rossburg, OH DLM Dream XXIX Dirt Super Late Models, DIRTcar Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 11th | - | 8th | - |
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| 6/10/2023 | Eldora Speedway - Rossburg, OH DLM Dream XXIX Dirt Super Late Models, DIRTcar Late Models | Results | | Ross Bailes (Dirt Super Late Models) | DNS | - | - | - |
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| 7/16/2023 | Wythe Raceway - Rural Retreat, VA Schaeffer's Oil Summer Nationals Rescheduled Dirt Super Late Models: Schaeffer's Oil Southern Nationals Street Stocks, Hornets, Limited Modified, Sport Compact, Dirt Mini Stocks | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 4th |
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| 7/22/2023 | Screven Motor Speedway - Sylvania, GA Dirt Super Late Models: Schaeffer's Southern Nationals Series with Schaeffer's Oil Southern Nationals Sport Compact: SCDRA - Sport Compact Dirt Racing Association Street Stocks, Dirt Crate Late Models, Crown Vic, 604 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 4th |
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| 8/5/2023 | Beckley Motor Speedway - Mount Hope, WV Beckley USA 100 Dirt Super Late Models: Southern All Stars B Modifieds, Hornets, Enduro, Mini Wedge, Kid Karts Dirt, Outlaw Hobby Stocks | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | 1st |
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| 8/10/2023 | Cherokee Speedway - Gaffney, SC Open Practice (All Divisions) Dirt Super Late Models, Dirt Big Block Modifieds | Results | | Ross Bailes (Dirt Big Block Modifieds) | - | - | - | - |
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| 8/11/2023 | Cherokee Speedway - Gaffney, SC American All-Star Late Model Series Night #1, AAS 604 LM, PS, X4, CV & YG V8 Pro Late Model: American All-Star Series Dirt Super Late Models, Hornets, Pony Stock, Pure Stock, Crown Vic, 604 Crate Late Models | Results | | Ross Bailes (Pro Late Model) | 5th | - | - | - |
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| 8/12/2023 | Cherokee Speedway - Gaffney, SC American All Star Late Model Series ($15,000) Night #2, AAS 604 LM,MMSA, 602 OWM & TB Pro Late Model: American All-Star Series Factory Stocks, A Modifieds, Supermodifieds, 604 Crate Late Models | Postponed |
| 8/13/2023 | Cherokee Speedway - Gaffney, SC Summer South Sizzler Dirt Super Late Models, Factory Stocks, A Modifieds, Supermodifieds, Pro Late Model | Results | | Ross Bailes (Pro Late Model) | - | - | 3rd | - |
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| 8/18/2023 | Richmond Raceway (KY) - Richmond, KY Thirty-Sixth Annual Butterball Memorial Prelims Dirt Super Late Models: Heart of America Ultimate Super Late Model Series Hornets, Super Stocks | Results | | Ross Bailes (Dirt Super Late Models) | 1st | - | - | - |
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| 8/19/2023 | Richmond Raceway (KY) - Richmond, KY Dirt Super Late Models: Heart of America Ultimate Super Late Model Series DIRTcar UMP Modifieds, Dirt Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 4th |
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| 8/25/2023 | Ultimate Motorsports & RV Park - Elkin, NC Open Practice Dirt Super Late Models, A Modifieds, B Modifieds, Dirt Late Models, Pro Late Model, Pony Stock, Dirt Mini Stocks, 602 Crate Late Models | Results | | Ross Bailes (Pony Stock) | - | - | - | - |
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| 8/26/2023 | Ultimate Motorsports & RV Park - Elkin, NC Grand Re-Opening: $7,500-To-Win ULTIMATE Super Late Models Dirt Super Late Models: ULTIMATE Southeast SLMS B Modifieds, 602 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | 5th | 19th |
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| 9/7/2023 | Eldora Speedway - Rossburg, OH 53rd annual World 100 Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 7th | - | 5th | - |
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| 9/8/2023 | Eldora Speedway - Rossburg, OH 53rd annual World 100 Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 6th | - | 2nd | - |
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| 9/9/2023 | Eldora Speedway - Rossburg, OH 53rd annual World 100 Dirt Super Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 8th | - | 16th | - |
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| 9/16/2023 | Cochran Motor Speedway - Cochran, GA Southern All Stars Dirt Super Late Models: Southern All Stars Sportsmans, Super Sports, Dirt Late Models, Enduro, Crown Vic, 602 Crate Late Models, 604 Crate Late Models | Results | | Ross Bailes (Dirt Late Models) | - | - | - | 12th |
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| 9/23/2023 | Fayetteville Motor Speedway - Fayetteville, NC Carlton Lamm "Big C" Memorial Race Carolina Clash Super Late Models $7500 to win Dirt Super Late Models: Carolina Clash Super Late Model Series A Modifieds, Street Stocks, Pro Legends, 602 Crate Late Models | Postponed |
| 9/29/2023 | Cherokee Speedway - Gaffney, SC Mike Duvall Memorial &V8 Nationals Night #1 (SAS SLMS $5,000/$500), RS, TB, PS, CV, YGV8 & 604 LM Dirt Super Late Models: Southern All Stars Factory Stocks, Stock Cars, Pony Stock, Pure Stock, Crown Vic, 604 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 18th |
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| 9/30/2023 | Cherokee Speedway - Gaffney, SC Mike Duvall Memorial & V8 Nationals Night #2 (SAS SLMS $12,000/$800) RS,TB, PS, ME 602 LM &OWM Dirt Super Late Models: Southern All Stars Factory Stocks, Stock Cars, A Modifieds, Pure Stock, 602 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | 8th |
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| 10/6/2023 | Swainsboro Raceway - Swainsboro, GA Southern Showcase Night One - $5,000-to-win HTF Super Dirt Series Dirt Super Late Models: Hunt The Front Super Dirt Series Stock Cars, Street Stocks, Roadsters, Dirt Crate Late Models, Crown Vic, 602 Crate Late Models, 604 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 6th | - | 3rd | 20th |
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| 10/7/2023 | Swainsboro Raceway - Swainsboro, GA Hunt the Front 23K to Win!!! Dirt Super Late Models: Hunt The Front Super Dirt Series Stock Cars, Street Stocks, Roadsters, Dirt Crate Late Models, Crown Vic, 602 Crate Late Models, 604 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 5th | - | 3rd | 18th |
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| 10/12/2023 | Tri-County Race Track - Brasstown, NC FK Rod Ends Tarheel 53 Dirt Super Late Models: Castrol FloRacing Night in America Hornets, 602 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 4th | - | - | 15th (DNF) |
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| 10/20/2023 | Eldora Speedway - Rossburg, OH 43rd Annual Dirt Track World Championship - Prelim Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds: Iron-Man Modified Series Dirt Late Models: Steel Block Late Model Series DIRTcar UMP Modifieds | Results | | Ross Bailes (Dirt Super Late Models) | - | - | - | - |
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| 10/21/2023 | Eldora Speedway - Rossburg, OH 43rd Annual Dirt Track World Championship Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models: Steel Block Late Model Series DIRTcar UMP Modifieds | Results | | Ross Bailes (Dirt Super Late Models) | 4th | - | 11th | - |
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| 10/31/2023 | Cherokee Speedway - Gaffney, SC Prelude to the Finals Dirt Super Late Models: XR Workin' Man Series 410 Sprints - Winged, Stock Cars, Dirt Big Block Modifieds | Results | | Ross Bailes (Dirt Super Late Models) | 5th | - | - | 8th |
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| 11/1/2023 | The Dirt Track at Charlotte - Concord, NC World of Outlaws World Finals 410 Sprints - Winged: World of Outlaws with 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) | - | - | - | - |
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| 11/2/2023 | The Dirt Track at Charlotte - Concord, NC World of Outlaws World Finals 410 Sprints - Winged: World of Outlaws with 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) | 7th | - | 7th | - |
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| 11/3/2023 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws with 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) | 13th | - | 14th | - |
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| 11/4/2023 | The Dirt Track at Charlotte - Concord, NC World of Outlaws World Finals 410 Sprints - Winged: World of Outlaws with 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) | 10th | - | 15th | - |
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| 11/18/2023 | Duck River Raceway Park - Shelbyville, TN The Gobbler $10K to win Super Late Models with $3K to win enduro Dirt Super Late Models: Hunt The Front Super Dirt Series Dwarf, Hornets, Enduro, Pony Stock, Pure Stock, CRUSA Modified Sportsman, 602 Crate Late Models | Results | | Ross Bailes (Dirt Super Late Models) | 2nd | - | - | 11th |
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