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Sandwiched between being released by Aberdeen in early September 2005 and joining Dundee, the striker had trials with both Dunfermline and Carlisle, but was unsuccessful in gaining a contract at either club. Craig actually scored against the Blues way back in the summer of 2003, scoring one of the goals that secured a 2-0 win for Motherwell over United in a pre-season friendly at Brunton Park.
Cumbrians boss at the time, Paul Simpson, had Craig down in Carlisle for a full week as he ran the rule over the Scotsman, Simpson telling the club website early on in the trial : "He looked sharp on Wednesday and he will stay with us until next week Tuesday. We're all pleased because he is clearly happy to be here. He is very keen to get on with things and he is looking forward to working with us."
That early promise wasn't enough for Craig to win a contract though and he linked up with Scottish First Division side Dundee on the 16th of September, signing a one-year contract with the Dees. On turning down a new two-year deal and leaving Dens Park to join Livingston the Blackburn-born forward commented : "Livingston offered me an extra year's security and it's my local club as well as I grew up and went to school in Broxburn. I'm pleased as I'll have the chance to work with manager John Robertson. In fact, he was probably the main factor in deciding to join the club. The manager was a forward as well which can only help me. He'll be the first manager who was a forward that I'll have worked under and he was an attacking player so hopefully I'll benefit from his experience."