Gailey was hired by the Yellow Jackets in 2002 to replace George O'Leary, who left to become head coach at the University of Notre Dame (O'Leary infamously resigned at Notre Dame after only 5 days). In his first five years at Georgia Tech, he had compiled a 37–27 record. Georgia Tech went to bowl games each year under Gailey, and won two: the 2003 Humanitarian Bowl (a 52–10 win over the University of Tulsa), and the 2004 Champs Sports Bowl (a 51–14 victory over Syracuse University). Gailey compiled six winning seasons in six years at the helm. However, he never defeated Tech's biggest rival, the University of Georgia, never won the ACC, never went to a BCS bowl, never won more than nine games, and never finished in the top 25. The 2006 season was his most successful at Georgia Tech, winning the ACC Coastal Division, but losing his last three games to rival UGA, Wake Forest in the ACC Championship Game, and West Virginia in the Gator Bowl.