The 1999 Jeep Oahu Bowl was a college football bowl game, played as part of the 1999-2000 bowl game schedule of the 1999 NCAA Division I-A football season. It was the 2nd Oahu Bowl. It was played on December 25, 1999, at Aloha Stadium in Honolulu, Hawaiʻi. The game matched the Hawaiʻi Warriors against the Oregon State Beavers, who were making their first bowl game appearance in 35 seasons, and was televised on ESPN. The victory marked the finale to one of the most memorable seasons in school history as Hawaiʻi had seen an improvement of nine wins over the previous winless season in 1998. Hawaiʻi won the 1999 contest 23-17.

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