Career
Kirkwood started his career with East Fife and joined Rangers under Graeme Souness in 1987 as a 19-year-old. After a disappointing spell in Glasgow he re-joined The Fifers on loan and signed for Hearts. He played with Airdrieonians and Raith Rovers before retiring.
Kirkwood was involved in youth development at Raith Rovers, Rangers and Ross county where he was Head of Youth Development for 5 years.
On 8 June 2011, Kirkwood was appointed manager of Scottish Highland League side Wick Academy. His first competitive game in charge ended in defeat against local amateur side Halkirk United and were knocked out of the North of Scotland Cup in the first round, in which the previous season Wick were losing finalists.
In his first Scottish Cup appearance as manager, Wick thumped Coldstream 9-1 but fell foul to fellow HL side Keith in the 2nd round. Wick finished the season in 8th place which was enough to qualify for the following season Scottish Challenge Cup.
2012-2013 kicked off against Kirkwood"s former side Raith Rovers in the Scottish Challenge Cup, a tightly contested game where Raith ran out 4-2 winners.
Kirkwood left Brora in July 2015 and was replaced by Richard Brittain.