He began his playing career with Kilmarnock, but made only one league appearance and spent time on loan to Queen of the South and St Johnstone before leaving the club in 2005.

In 2010, Samson joined St Mirren, where he played for three years and won the Scottish League Cup in 2013.

Samson began his career with Kilmarnock and made his senior debut on 3 January 2004, in a Scottish Premier League match away to Aberdeen.

Outside the Old Firm, Samson and Motherwell 'keeper Darren Randolph kept the most clean sheets in the division, despite St Mirren finishing 8th in the table.

On 17 March 2013, Samson played as St Mirren beat Hearts 3–2 to win the League Cup.

[15] On 6 August 2015, Samson left Kilmarnock, agreeing a release from his contract having lost his first team place to new signing Jamie MacDonald.

[29] Samson also registered as a player with Hibs, and was listed as a substitute for a League Cup match with Brora Rangers on 7 October.

[31] After leaving Hibernian, Samson signed a short-term deal with Aberdeen in a player-coaching role due to an injury crisis at the club.