[2] He averaged 12.1 points and 3.2 rebounds in 28 games in his first season, earning himself North Atlantic Conference All-Rookie Team honors.
[3] As a sophomore playing for the Hawks in 1996–97, Bailey was considered the team's super-sub after a preseason ankle injury moved him to the bench.
[3] As a junior in 1997–98, Bailey earned first-team All-North Atlantic Conference honors after averaging 20.1 points and 5.0 rebounds in 27 games.
[5] As co-captain his senior year in 1998–99, Bailey earned second-team All-America East Conference honors after averaging 20.1 points and 4.4 rebounds in 27 games.
[3] He scored 1,086 combined points as a junior and senior, and with his 20-point-per-game average both years, he became only the second player to do so in consecutive seasons in the Division I era.
[10] In March 2005, after a three-year hiatus from basketball, Bailey returned to Portugal to play out the 2004–05 season with FC Porto.
[15] In late December, he missed a two-game North Queensland road trip due to an ankle injury.
[21][22] Bailey spent the 2008–09 season in Russia playing for Sibirtelecom Lokomotiv Novosibirsk, averaging 11.5 points, 3.2 rebounds, 2.8 assists and 2.1 steals in 18 games.
[33][34] Bailey served as an assistant coach with the Otago Nuggets during the 2020 New Zealand NBL season,[34][35] helping them win the championship.