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| 5/30/2020 | Rice Lake Speedway - Rice Lake, WI 68th Season Opener: Five Class program Best Appearing Car Judging WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Leonard Osterberg Jr (WISSOTA Pure Stock) | 5th | - | - | 16th |
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| 6/6/2020 | Rice Lake Speedway - Rice Lake, WI WISSOTA Late Models plus Supers, Streets, MWM, and Pures no Mods DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Leonard Osterberg Jr (WISSOTA Pure Stock) | 6th | - | - | 16th (DNF) |
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| 6/27/2020 | Rice Lake Speedway - Rice Lake, WI 5 Class program WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Leonard Osterberg Jr (WISSOTA Pure Stock) | 5th | - | - | 11th |
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| 7/2/2020 | Rice Lake Speedway - Rice Lake, WI Fire Cracker Special, Barron County Relay at the Races, Five Classes WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Leonard Osterberg Jr (WISSOTA Pure Stock) | 7th | - | - | 19th (DNF) |
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| 7/11/2020 | Rice Lake Speedway - Rice Lake, WI Five Class Program Plus Street Stock Bonus Night WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Leonard Osterberg Jr (WISSOTA Pure Stock) | 8th (DNF) | - | - | 12th |
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| 8/15/2020 | Rice Lake Speedway - Rice Lake, WI Hall of Fame Night - Five Class Program WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Leonard Osterberg Jr (WISSOTA Pure Stock) | 7th | - | - | 10th |
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| 8/22/2020 | Rice Lake Speedway - Rice Lake, WI Bike Races - Five Class Program Plus Kid's Night WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Leonard Osterberg Jr (WISSOTA Pure Stock) | 7th | - | - | 15th |
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