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| 1/7/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Points Race #7 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw, 125 Winged Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | 3rd | - | - | 10th |
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| 1/8/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Points Race #8 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw, 125 Winged Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | 7th | - | - | 7th |
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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 | | Jessie Henry (250 Winged Outlaw Heavy) | 6th | - | 1st | 10th |
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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 | | Jessie Henry (250 Winged Outlaw Heavy) | 5th | - | 3rd | 10th |
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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 | | Jessie Henry (250 Winged Outlaw Heavy) | 5th | - | - | 6th |
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| 2/4/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Points Race #11 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw, 125 Winged Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | 5th | - | - | 5th |
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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 | | Jessie Henry (250 Winged Outlaw Heavy) | 5th | - | - | 4th |
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| 11/7/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Prelude to the Timber 50 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | 4th | - | - | 3rd |
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| 11/8/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR QRC Timber 50 - Practice Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | - | - | - | - |
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| 11/9/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR QRC Timber 50 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | 3rd | - | 4th | 8th |
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| 11/10/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR QRC Timber 50 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | 2nd | - | 2nd | 10th |
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| 11/11/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR QRC Timber 50 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | - | - | 3rd | 8th |
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| 11/24/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Points Race #1 - (Turkey Shootout) Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | 4th | - | - | 7th |
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| 11/25/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Points Race #2 - (Turkey Shootout) Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | 3rd | - | - | 6th |
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| 12/8/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Points Race #3 Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | 3rd | - | - | 4th |
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| 12/29/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Points Race #4 Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | 1st | - | - | 13th (DNF) |
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| 12/30/2023 | Roseburg Outlaw Kart Racing - Roseburg, OR Points Race #5 Restricted Box Stock, Unrestricted Box Stock, Flat RWYB, 250 Winged Outlaw Heavy, 500 Winged Open Outlaw Heavy, 500 Winged Open Outlaw | Results | | Jessie Henry (250 Winged Outlaw Heavy) | 5th | - | 2nd | 8th |
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