Middlesbrough Kennedy started his career at
Middlesbrough. He made his debut for the
North East of England club in the
2004–05 season, in a game against
Fulham. He made six appearances, four of which were as substitute, in
2005–06, and participated in Middlesbrough's
UEFA Cup run in the season against
Litex Lovech, playing the full game. Kennedy was handed a two-year contract in 2005 by manager
Steve McClaren. He joined
Scottish Football League club
Livingston in August 2007 on a six-month loan deal.
Darlington He made another loan move in 2008, this time to
League Two side
Darlington. On 10 May 2008, Kennedy scored the first goal in the League Two play-off semi-final first leg between Darlington and
Rochdale. Darlington went on to win the match 2–1. However, in the second leg he missed his kick in a penalty shoot-out, sending Rochdale through to the play-off final. On 30 May 2008 Kennedy signed a two-year permanent deal with Darlington. He followed these up with goals against
MK Dons,
Huddersfield Town and
Charlton Athletic and ended the season with 4 goals. He played his final game for the club on 27 April 2013, helping Rochdale to a 1–0 win against
Plymouth Argyle. He left having made over 200 appearances for the club during a four-year spell and was part of the
2009–10 promotion winning team.
Bradford City On 2 July 2013, Kennedy signed for
Bradford City on a free transfer following the expiry of his contract, on a two-year deal. He had almost signed for the club during the previous transfer window, and rejected the chance to stay at Rochdale as well as an offer from
Hartlepool United to sign with The Bantams. He made his league debut on 5 October in a 2–0 win away to
Walsall.
Rochdale Return On 24 January, Kennedy moved to
Rochdale on loan until the end of the 2013–14 season.
Carlisle United On 12 March 2015, Kennedy completed a one-month loan deal to
League Two club
Carlisle United. He made a bright start to his Carlisle career, scoring his first goal on his second start for the Blues, a 2–0 away victory over Northampton. In May 2015 it was announced Kennedy would leave Bradford City at the end of the season. Kennedy returned to Carlisle the same week signing a permanent two-year deal He was released by Carlisle at the end of the 2018–19 season.
Hartlepool United Following a successful trial, Kennedy signed for
Hartlepool United on 18 July 2019.
Spennymoor Town Kennedy signed for
National League North side
Spennymoor Town on loan till the end of the season Kennedy became a player-coach at Spennymoor in May 2021. On 11 January 2022, Kennedy joined
Northern Premier League Division One East side
Marske United on a two-month loan deal.
Marske United On 25 February 2022, Kennedy joined
Northern Premier League Division One East side
Marske United on a permanent deal. ==Career statistics==