Career
Keenan started his career with Premier League club Chelsea. Keenan was given a four-year contract in 2002 and was seen as a "hot prospect" by Claudio Ranieri. He suffered a broken leg soon afterwards, however, which kept him out of action for most of the 2002-2003 season.
He made one further appearance in a league match, but fell out of favour after Jose Mourinho became manager and was loaned out.
Keenan then signed for Melbourne Victory Football Club, playing as a left wingback for the 2007-2008 Australian champions. He can also play anywhere across midfield.
Keenan signed for Scottish Premier League side Hibernian in July 2008. He scored his first goal for the club in a Scottish League Cup defeat against Morton, but he struggled to hold down a first team place, making only 16 appearances.
When John Hughes replaced Mixu Paatelainen as manager before the start of the 2009-2010 season, Keenan was told that he was free to find a new club
Keenan was released from his contract at the end of August. Keenan signed a contract with South Melbourne on 9 December 2009 to play in the upcoming VPL season. He returned to the A-League on loan with Adelaide United for the 2010-2011 season as an injury replacement player for injured Nigel Boogaard.