| | Heat | Dash | B Feature | A Feature |
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| 1/21/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Winter Showdown - (Night #1) Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw, 125 Winged Outlaw | Results | | Ryan Simmons (125 Winged Outlaw) | 4th | - | - | 2nd |
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| 1/22/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Winter Showdown - (Night #2) Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw, 125 Winged Outlaw | Results | | Ryan Simmons (125 Winged Outlaw) | 3rd | - | - | 4th |
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| 1/28/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Points Race #10 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw, 125 Winged Outlaw | Results | | Ryan Simmons (125 Winged Outlaw) | 4th | - | - | 4th |
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| 2/11/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Points Race #12 Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw, 125 Winged Outlaw | Results | | Ryan Simmons (125 Winged Outlaw) | 4th | - | - | 2nd |
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