Kenneth, who was brought up in Dundee, played for Dundee United Social Club and St.Josephs, before he returned with a second spell at Dundee United Social Club. Kenneth, who is a keen Dundee United supporter and came through the
Jim McLean School of Excellence, made his debut for United in February 2005, playing in the 3–0
Scottish Cup win at
Queen of the South. Playing in the remaining thirteen games of the season, Kenneth's introduction to league football saw eleven goals conceded in just four games. However, following the Cup semi-final win over
Hibernian, his contribution helped United concede just four goals in the final six league games. Kenneth was part of the United team who lost the
2005 Scottish Cup Final against
Celtic. Kenneth signed a new contract in October 2006, taking him to 2010. In March 2007, Kenneth moved to
Cowdenbeath on loan for the remainder of the season, after losing his place in the United first team. Kenneth regained his place in the team in early 2008, playing in the
League Cup final defeat to
Rangers. In mid-January 2010, Dundee United rejected a £75,000 bid from
Blackpool for Kenneth, stating that the offer was "ridiculously small". On 29 January, and with the
transfer window coming to a close, Blackpool manager
Ian Holloway confirmed that the club had made a vastly improved offer for Kenneth. The offer believed to be in the region of £500,000, was rejected by Dundee United, who after a fantastic 2009–10 season, valued the player at around £2m. Kenneth helped Dundee United get to the
2010 Scottish Cup Final and started in
The Terrors 3–0 win over
Ross County. Kenneth stated in November 2011 that he would be leaving United at the end of the 2011–12 season, in the hope of earning a move to the
Football League Championship. Kenneth played as a trialist for
Airdrie United in a closed doors friendly against
Rangers in July 2012.
Bristol Rovers At the end of July 2012, he signed a three-year deal with
League Two side
Bristol Rovers. He made his Bristol Rovers début in a 1–1 draw at
Plymouth Argyle on 18 September 2012, playing the full 90 minutes of the match. He made his home debut on 22 September 2012 in a 1–1 draw to
Fleetwood Town. He scored his first goal for Bristol Rovers on 6 October 2012, against
Northampton Town, in a 3–1 win. After an injury-plagued 16 months, in December 2013 Bristol Rovers announced Kenneth had left the club by mutual consent.
Later career On 12 February 2014, Kenneth signed for
Scottish League One club
Brechin City until the end of the season. On 21 August 2014, he signed for
Junior club
Carnoustie Panmure on a two-year deal. On 11 January 2015, it was announced that Kenneth had signed for Australian club
Adamstown Rosebud playing in the
Northern NSW NPL for the 2015 season. He then joined Latvian club
Skonto Riga in July 2015 before returning to junior football in Scotland, signing for
Forfar Albion in November 2015. On 15 February 2016, Kenneth signed a long-term contract with
Lowland Football League side
Selkirk. As of 2017, he was pursuing a career outside of football. On 5 August 2018, Kenneth signed for
Lochee United. ==International career==