He scored with an overhead kick on his home debut against Hereford United after a headed pass from Gary Wright, and although sent off 3 more times that season (for which he received an 8 match ban) his ability to lead the attack made him an unlikely favourite of the crowd as Torquay made the play-offs and got further than usual in the cup competitions.
In August 1988 he left Plainmoor for Belgian side KVV Overpelt (costing £13,000) after 24 league games for the Gulls, scoring 4 times, but returned to Torquay on loan in December 1989.
Following a spell playing in South Africa, in October 1990 he returned to Chesterfield, with a fee of £14,500 resembling a reasonable piece of business by the Belgian side.
Whilst playing for Cove Rangers he began working as a sales executive for an office equipment business.
Now living in Glasgow, alongside coaching another side, Caldwell has made two substitute appearances for Cardonald AC, scoring the winning goal in his most recent outing.