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| 5/19/2023 | Ohsweken Speedway - Ohsweken, ON 360 Sprints - Winged, DIRTcar UMP Modifieds, Asphalt Mini Stocks, Street Stocks, Winged Crate Sprints | Results | | Darren Dryden (360 Sprints - Winged) | 5th | - | - | 10th |
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| 5/20/2023 | Brighton Speedway - Brighton, ON $2,598-to-win Paul Pekkonen Memorial 360 Sprints - Winged: Southern Ontario Sprints | Rain Out |
| 5/26/2023 | Ohsweken Speedway - Ohsweken, ON Duel on the Dirt Home Track Race #1 360 Sprints - Winged, Asphalt Mini Stocks, Street Stocks, Winged Crate Sprints | Results | | Darren Dryden (360 Sprints - Winged) | 3rd | - | - | 15th |
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| 5/27/2023 | Southern Ontario Motor Speedway - Merlin, ON 360 Sprints - Winged: Southern Ontario Sprints | Results | | Darren Dryden (360 Sprints - Winged) | 4th | - | - | 5th |
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| 6/2/2023 | Ohsweken Speedway - Ohsweken, ON Wall of Fame Night 360 Sprints - Winged, Asphalt Mini Stocks, Street Stocks, Winged Crate Sprints | Results | | Darren Dryden (360 Sprints - Winged) | 4th | - | - | 4th |
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| 6/10/2023 | Brighton Speedway - Brighton, ON $2,498-to-win Paul Pekkonen Memorial 360 Sprints - Winged: Southern Ontario Sprints | Results | | Darren Dryden (360 Sprints - Winged) | 2nd | - | - | 2nd |
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| 6/24/2023 | Merrittville Speedway - Thorold, ON Gary Cunningham Memorial 360 Sprints - Winged: Southern Ontario Sprints Asphalt Mini Stocks, Stock Cars, Street Stocks, Dwarf | Results | | Darren Dryden (360 Sprints - Winged) | 2nd | - | - | 23rd (DNF) |
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| 6/30/2023 | Ohsweken Speedway - Ohsweken, ON Friday Night Excitement 360 Sprints - Winged, Asphalt Mini Stocks, Street Stocks, Vintage Modifieds, Winged Crate Sprints | Results | | Darren Dryden (360 Sprints - Winged) | 4th | - | - | 9th |
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| 7/7/2023 | Ohsweken Speedway - Ohsweken, ON Drive Safe Ride Safe Bicycle Night Winged Crate Sprints: Action Sprint Tour 360 Sprints - Winged, Asphalt Mini Stocks, Street Stocks | Results | | Darren Dryden (360 Sprints - Winged) | 3rd | - | - | 6th |
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| 7/9/2023 | Humberstone Speedway - Port Colborne, ON Sprint Car Summer Heat 360 Sprints - Winged: Southern Ontario Sprints Street Stocks, DIRTcar Sportsman Modifieds, Mod Lites, Dirt Mini Stocks | Results | | Darren Dryden (360 Sprints - Winged) | 1st | - | - | 4th |
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| 7/14/2023 | Ohsweken Speedway - Ohsweken, ON $4,000-to-win Tammy Ten/Little Ben Night 360 Sprints - Winged: Southern Ontario Sprints Asphalt Mini Stocks, Street Stocks, Winged Crate Sprints | Results | | Darren Dryden (360 Sprints - Winged) | 1st | - | - | 9th |
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| 7/28/2023 | Ohsweken Speedway - Ohsweken, ON Christmas in July 360 Sprints - Winged, Asphalt Mini Stocks, Street Stocks, Winged Crate Sprints | Results | | Darren Dryden (360 Sprints - Winged) | 3rd | - | - | 2nd |
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| 7/29/2023 | Southern Ontario Motor Speedway - Merlin, ON 360 Sprints - Winged: Southern Ontario Sprints | Results | | Darren Dryden (360 Sprints - Winged) | 3rd | - | - | 7th |
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| 8/11/2023 | Ohsweken Speedway - Ohsweken, ON Sportsman Shootout 360 Sprints - Winged, Asphalt Mini Stocks, Street Stocks, DIRTcar Sportsman Modifieds | Results | | Darren Dryden (360 Sprints - Winged) | 1st | - | - | 5th |
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| 8/14/2023 | Ohsweken Speedway - Ohsweken, ON Pintys 360 Sprints - Winged: Southern Ontario Sprints Winged Crate Sprints: Action Sprint Tour | Results | | Darren Dryden (360 Sprints - Winged) | - | - | - | 15th |
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| 8/15/2023 | Ohsweken Speedway - Ohsweken, ON Pintys 360 Sprints - Winged: Southern Ontario Sprints Winged Crate Sprints: Action Sprint Tour | Results | | Darren Dryden (360 Sprints - Winged) | - | - | 2nd | 7th |
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| 8/18/2023 | Ransomville Speedway - Ransomville, NY 716 Night 360 Sprints - Winged: Southern Ontario Sprints DIRTcar Sportsmans, Factory Stocks, A Modifieds, Street Stocks | Results | | Darren Dryden (360 Sprints - Winged) | 1st | - | - | 6th |
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| 9/1/2023 | Ohsweken Speedway - Ohsweken, ON Back to School Backpack Night 360 Sprints - Winged, Asphalt Mini Stocks, Street Stocks, Winged Crate Sprints | Results | | Darren Dryden (360 Sprints - Winged) | 2nd | - | - | 9th |
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| 9/8/2023 | Ohsweken Speedway - Ohsweken, ON Championship Friday 360 Sprints - Winged, Asphalt Mini Stocks, Street Stocks, Winged Crate Sprints | Results | | Darren Dryden (360 Sprints - Winged) | 5th | - | - | 16th |
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| 9/9/2023 | Merrittville Speedway - Thorold, ON $3,000 To win Nitro Super Series Race 360 Sprints - Winged: Southern Ontario Sprints Asphalt Mini Stocks, Sportsmans, Street Stocks, Dwarf | Results | | Darren Dryden (360 Sprints - Winged) | 2nd | - | - | 1st |
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| 9/15/2023 | Ohsweken Speedway - Ohsweken, ON CSCN 360 Sprints - Winged: Southern Ontario Sprints Winged Crate Sprints: Action Sprint Tour Asphalt Mini Stocks, Street Stocks | Results | | Darren Dryden (360 Sprints - Winged) | 2nd | - | - | 2nd |
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| 9/16/2023 | Ohsweken Speedway - Ohsweken, ON CSCN 360 Sprints - Winged: Empire Super Sprints with Southern Ontario Sprints Winged Crate Sprints: Action Sprint Tour | Results | | Darren Dryden (360 Sprints - Winged) | 3rd | - | - | 22nd |
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| 9/29/2023 | Humberstone Speedway - Port Colborne, ON Fall Classic Night #1 360 Sprints - Winged: Southern Ontario Sprints Winged Crate Sprints: Action Sprint Tour Street Stocks, DIRTcar Sportsman Modifieds, Dirt Mini Stocks, 604 Crate Late Models | Results | | Darren Dryden (360 Sprints - Winged) | 4th | - | - | 12th |
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| 9/30/2023 | Humberstone Speedway - Port Colborne, ON Fall Classic 360 Sprints - Winged: Southern Ontario Sprints Winged Crate Sprints: Action Sprint Tour Street Stocks, DIRTcar Sportsman Modifieds, Mod Lites | Results | | Darren Dryden (360 Sprints - Winged) | 4th | - | - | 9th |
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| 10/14/2023 | Brockville Ontario Speedway - Elizabethtown, ON Fall Nationals 360 Sprints - Winged: Southern Ontario Sprints DIRTcar Sportsmans: DIRTcar Sportsman Series Race DIRTcar 358 Modifieds: DIRTcar 358 Modified Series Street Stocks, Vintage Modifieds | Results | | Darren Dryden (360 Sprints - Winged) | 2nd | - | - | 4th |
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