Midfielder McSkimming was born in Stranraer on May 29th 1970 and started his football career at Dens, coming through the youth ranks to make his debut for Jocky Scott’s side at home to Motherwell on April 6th 1988. It was his only appearance of that season and despite making the first team photo at the start of following campaign, he failed to make a single appearance under new manager Dave Smith who took over from Scott after he moved north to Pittodrie.
Smith’s reign was short lived and his successor Gordon Wallace gave McSkimming some top-flight experience during season 1989/90 when he made eight starts and one substitute appearance which included matches against both sides of the Old Firm and two matches against Dundee United in the Scottish Cup.
Unfortunately, Dundee were relegated at the end of that campaign but in the First Division, McSkimming became a regular in the side as they tried to bounce back to the top flight at the first attempt. Shaun scored his first goal for The Dee on September 1st in a 1-0 win at Morton in the first away game of the season and again scored the only goal away at Meadowbank in December and in the earlier 2-1 home defeat to Thistle the previous month.
Defeats to the likes of Meadowbank however would cost the Dark Blues dear because at the end of the season Dundee would miss out on the Scottish League First Division title by two points behind Falkirk and miss out on a promotion by a point behind Airdrieonians.
This therefore had financial implications at the club, meaning some players had to be sold and Keith Wright was the highest profile departure with a £500,000 move to Hibernian. Following ‘the Mongoose’ out the door was promising 21 year old Shaun McSkimming who surprisingly moved to fellow First Division club Kilmarnock for a fee of £40,000.
McSkimming faced his old side four times in his debut Killie season when The Dee won 2-1 twice home and away, drew 1-1 at Dens on Jim Leighton and Simon Stainrod’s debut and lost 2-0 at Rugby Park with three games to go.
That result did not however stop Dundee winning the Scottish League First Division title and promotion back to the top flight with Kilmarnock finishing four points behind the Dark Blues in fourth. The following season however, with the same 54 points total, Kilmarnock won promotion back to the Premier Division as runners-up to Raith Rovers and they have been in the top flight ever since.
McSkimming spent three seasons at Rugby Park, scoring 12 times in over 100 league games and after helping newly promoted Killie retain their top flight status at his old club’s expense and winning a Scotland B cap against Wales in Wrexham, moved to Motherwell in the summer of 1994.
Shaun stayed at Fir Park for four years, finishing as runners-up in the Premier Division in his first season under manager Tommy McLean, (Motherwell’s best finish since 1934) and would in total score seven times in 63 league appearances for the Steelman.
In the summer of 1998, McSkimming returned to his old club Dundee when manager Jocky Scott signed him as part of the ‘Motherwell Four’. With Dundee newly promoted back into the top flight, into inaugural Scottish Premier League, Scott, who had signed him as a youngster, raided the Fir Park club to sign Eric Garcin, Willie Falconer, Tommy Coyne, alongside Shaun.
Wearing squad number 21, McSkimming made his second debut in the first SPL game of the season against Aberdeen at Dens, after they had raised the First Division winning flag. He would be a regular that term, featuring 30 times as the Dark Blues not only stayed up but also finished fifth, their joint highest position since winning the Scottish title in 1962.
McSkimming scored his first goal since his return against Dundee United in a New Year derby at Dens and would score the winner against his old side Kilmarnock in a 2-1 home win at the end of April but both terracings behind the goals had already been demolished in preparations for the new stands to be built in the summer.
McSkimming swapped to squad number 12 for the second SPL season and again was a regular with four goals in 31 appearances. In the summer of 2000 however, it was all change on Sandeman Street with Ivano Bonetti replacing Jocky Scott in the hot seat and Shaun was used sparingly by the Italian, starting just seven times and coming off the bench on a further seven occasions.
One of those starts was the famous ‘Juan-Two-Three Derby’ when Argentinean striker Juan Sara wrote his name into Dark Blue folklore with a hat-trick against the Arabs in a 3-0 win at Dens. In McSkimming’s three-year second spell he played in three derby wins and one draw (when Adamzcuk equalised in injury time after being 2-0 down) while The Dee enjoyed another two wins over United during his time at Dens.
After playing the exact number of league games as he had done in his Fir Park days, McSkimming left Dundee at the end of the 2000/01 season to spend a year in the United States with Atlanta Silverbacks before returning to Scotland and joining Peterhead.