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| 4/1/2023 | Lawton Speedway - Lawton, OK Season Opener Non-Winged Sprints, Pony Stock, USRA Limited Mods, USRA Modifieds, USRA Factory Stocks, IMCA RaceSaver Sprint Car | Results | | Ray W Caldwell III (Pony Stock) | 6th | - | - | 12th (DNF) |
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| 5/6/2023 | Lawton Speedway - Lawton, OK Non-Winged Sprints: United Sprint League Pony Stock, USRA Limited Mods, USRA Factory Stocks | Results | | Ray W Caldwell III (Pony Stock) | 4th | - | - | 8th |
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| 5/20/2023 | Lawton Speedway - Lawton, OK 410 Sprints - Winged: ASCS Elite Outlaw Sprints Pony Stock, USRA Limited Mods, USRA Factory Stocks | Results | | Ray W Caldwell III (Pony Stock) | DNS | - | - | 9th |
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| 5/27/2023 | Lawton Speedway - Lawton, OK COMANCHE COUNTY NIGHT Pony Stock, USRA Limited Mods, USRA Factory Stocks, IMCA RaceSaver Sprint Car | Results | | Ray W Caldwell III (Pony Stock) | DNS | - | - | 13th |
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| 6/22/2023 | Lawton Speedway - Lawton, OK 360 Sprints - Winged: ASCS National Midgets, Winged Outlaw, Pony Stock, USRA Limited Mods, USRA Factory Stocks | Results | | Ray W Caldwell III (Pony Stock) | 3rd | - | - | 6th |
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| 6/24/2023 | Lawton Speedway - Lawton, OK TEXAS NIGHT Non-Winged Sprints, Pony Stock, USRA Limited Mods, USRA Factory Stocks | Results | | Ray W Caldwell III (Pony Stock) | 2nd | - | - | 11th (DNF) |
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| 7/1/2023 | Lawton Speedway - Lawton, OK 7/1 EVENT Pony Stock, USRA Limited Mods, USRA Modifieds, USRA Factory Stocks, IMCA RaceSaver Sprint Car | Results | | Ray W Caldwell III (Pony Stock) | 3rd | - | - | 10th (DNF) |
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| 7/15/2023 | Lawton Speedway - Lawton, OK 2ND ANNUAL ROB BLAND MEMORIAL RACE EVENT Pony Stock, USRA Limited Mods, USRA Modifieds, USRA Factory Stocks | Results | | Ray W Caldwell III (Pony Stock) | 3rd | - | - | 6th |
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| 7/22/2023 | Lawton Speedway - Lawton, OK 7/22 EVENT Non-Winged Sprints, Pony Stock, USRA Limited Mods, USRA Factory Stocks, IMCA RaceSaver Sprint Car | Results | | Ray W Caldwell III (Pony Stock) | 1st | - | - | 9th |
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| 7/29/2023 | Lawton Speedway - Lawton, OK 7/29 EVENT Non-Winged Sprints, Pony Stock, USRA Limited Mods, USRA Modifieds, USRA Factory Stocks | Results | | Ray W Caldwell III (Pony Stock) | 6th | - | - | 6th |
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| 8/5/2023 | Lawton Speedway - Lawton, OK BACK TO SCHOOL BASH & BICYCLES RACES Pony Stock, USRA Limited Mods, USRA Factory Stocks, IMCA RaceSaver Sprint Car | Results | | Ray W Caldwell III (Pony Stock) | 6th | - | - | 8th |
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| 8/19/2023 | Lawton Speedway - Lawton, OK Champ 360 Sprints - Winged: Oil Capital Racing Series Pony Stock, USRA Limited Mods, USRA Factory Stocks | Results | | Ray W Caldwell III (Pony Stock) | 4th | - | - | 5th | | Ray W Caldwell III (USRA Factory Stocks) | 6th (DNF) | - | - | 9th |
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| 8/26/2023 | Lawton Speedway - Lawton, OK CHAMPIONSHIP FINALS Non-Winged Sprints, Pony Stock, USRA Limited Mods, USRA Modifieds, USRA Factory Stocks, IMCA RaceSaver Sprint Car | Results | | Ray W Caldwell III (Pony Stock) | 4th | - | - | 5th |
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| 9/29/2023 | Lawton Speedway - Lawton, OK 31ST ANNUAL WINTER NATIONALS Non-Winged Sprints, Pony Stock, USRA Limited Mods, USRA Modifieds, USRA Factory Stocks, IMCA RaceSaver Sprint Car | Results | | Ray W Caldwell III (Pony Stock) | DNS | - | - | 9th | | Ray W Caldwell III (USRA Factory Stocks) | 6th (DNF) | - | - | 11th (DNF) |
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| 9/30/2023 | Lawton Speedway - Lawton, OK 31ST ANNUAL WINTER NATIONALS & LANNY EDWARDS MEMORIAL VINTAGE RACE EVENT Non-Winged Sprints, Pony Stock, USRA Limited Mods, USRA Modifieds, USRA Factory Stocks, IMCA RaceSaver Sprint Car | Results | | Ray W Caldwell III (Pony Stock) | 1st | - | - | 16th | | Ray W Caldwell III (USRA Factory Stocks) | 7th | - | - | 9th |
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