McSkimming signed for Dundee at the start of the 1987-88 season and remained at Dens Park for 4 years, where he played in 24 league matches and scored 3 league goals. In the close season of 1991, McSkimming signed for East Ayrshire club Kilmarnock, where he stayed for three years. McSkimming's first match for Killie was at Rugby Park on 10 August 1991 versus Stirling Albion. McSkimming proved a fair acquisition, scoring some fine goals that included a brilliant solo effort at East End Park versus Dunfermline Athletic and also the winner in a 2–1 home win versus Killie'sSouth Ayrshire rivals Ayr United in the Scottish Cup of season 1993-94. McSkimming's last match for Killie was on 29October 1994 versus Motherwell at Fir Park. McSkimming should arguably have scored more goals at Rugby Park but by the time he was due to depart he was being utilised as a wing back. McSkimming played in 113 league matches and scored 9 league goals.
McSkimming signed for Motherwell in early November 1994 for £300,000. There was some disquiet when he was quoted in the media saying he had joined a bigger club to win medals. Whether he had actually said this is up for debate but McSkimming did not win any silverware at Fir Park and was always taunted by the Killie supporters whenever the two clubs played against each other. In his four years at Well, McSkimming played in 64 league matches and scored 7 league goals. McSkimming then re-signed for his first club Dundee in the close season of 1998, where he stayed for three years, playing in 63 league matches and scoring 4 goals. In July 2001, McSkimming moved to the USA to join the Atlanta Silverbacks for six months. On his return to Scotland in January 2002, McSkimming had a short spell at Peterhead, playing in 9 league matches and scoring one goal. After leaving at the end of the 2001-02 season, McSkimming re-signed for the Blue Toon at the start of the 2002-03 season, where he played in 57 league matches without scoring any goals in his second spell. McSkimming then retired from playing to take up a coaching post with Peterhead in the close season of 2005.
