During his freshman year, Weekes played an integral role in the Columbia Lions' 1899 upset of the Yale Bulldogs at Manhattan Field. The heavily favored Bulldogs entered the game undefeated with a 5-0 record. While notching five consecutive shutouts in those games, Yale had scored a combined 115 points (for an average of 23 points per game.) At the time, Yale carried a reputation as a perennial powerhouse. In stark contrast, Columbia had just resumed playing football that season after a seven-year absence from the game (1892-1898).