Season 1 of Hollywood Squares premiered on Sep 14, 1998
Season 2 of Hollywood Squares premiered on Sep 13, 1999
Season 3 of Hollywood Squares premiered on Sep 04, 2000
Season 4 of Hollywood Squares premiered on Sep 10, 2001
Season 5 of Hollywood Squares premiered on Sep 16, 2002
Season 6 of Hollywood Squares premiered on Sep 08, 2003