A boyhood Glentoran fan, Craigan started his career in Scotland with Motherwell in 1994 when he was signed by Alex McLeish. However, after only twenty-six appearances, he was released on a free transfer. He signed for Scottish Second Division club Partick Thistle in 2000 and helped them back to the Scottish Premier League, making 121 appearances. After his contract expired in 2003, he returned to Motherwell, who were then managed by former England international Terry Butcher.
Since then, Craigan has been an integral part of Motherwell's steady progress in the league. Craigan has since gone on to become Motherwell's most capped player. He works for BBC Radio Scotland, also commentated on some European matches for Setanta Sports and ESPN. Craigan is a regular pundit on Sky Sports News Radio, rounding up the weekly hot topics in the SPL.
On January 2008, Craigan was made club captain of Motherwell, taking over from Phil O'Donnell, who died after collapsing on the pitch during a match against Dundee United on 29 December 2007.
In June 2009, Craigan was appointed the player-caretaker manager of Motherwell while the club looked for a replacement for Mark McGhee, who departed for Aberdeen. This temporary appointment ended when Jim Gannon was hired as the new manager. He endured a troubled relationship with Gannon, featuring in only seven of the seventeen league games he was in charge at Motherwell after being publicly criticised by the manager, but returned to regular first-team action under Craig Brown. On 16 April 2011 Craigan scored his first goal since 2006 with a header to open the scoring in the Scottish Cup semi-final against St Johnstone, which Motherwell won 3-0 to advance to the 2011 Scottish Cup Final.
On 9 June 2011, Craigan signed a new one-year contract at Motherwell. Craigan was awarded a testimonial match, against his former club Partick Thistle. He scored the only goal of the game, on 13 July 2011. On 9 May 2012, Craigan announced that he would retire after Motherwell's last game of the 2011–12 Scottish Premier League season.
Craigan is Motherwell's record cap holder, having received 54 caps for Northern Ireland. Craigan played in their 1–0 victory against England in September 2005 and the 3–2 win over Spain a year later. He captained his country on their end of season tour in 2010 against Turkey and Chile and continued as captain against Montenegro on 11 August 2010. His 50th cap came in a surprise victory away to Slovenia on 3 September 2010, in their first game of the Euro 2012 campaign. On 19 July 2011, Craigan announced his retirement from International football, earning 54 caps, the last of those coming against Slovenia.
Craigan has made steady strides into management. As well as being caretaker manager for Motherwell in 2009, he was named assistant manager of the Northern Ireland Under-19 squad on 11 October 2012. He also continued working as a football pundit for radio and television. In July 2015, Craigan was appointed manager of Motherwell's under-20 team. After manager Ian Baraclough left the club in September, Craigan was put in temporary control of the first team.`As of 13 May 2012
As of August 2011