Among Jennings's most notable upsets was the ending of Bud Wilkinson's 74-straight conference victories. The Cornhuskers beat the Oklahoma Sooners, 17–14, at Nebraska's 1959 homecoming game on Halloween. Jennings followed up a second consecutive win the following year with a 25–21 victory in Norman. The 1959 win was the first for Nebraska since 1942, and the 1959–1960 wins were the first consecutive victories over the Sooners since 1939–1942. Jennings died on June 8, 2002 at the age of 84 at his home in Lawrence, Kansas after suffering from prostate cancer.