Chisholm succeeded McCall as manager of Dundee United in 2005, and guided the club to the 2005 Scottish Cup Final, which they lost 1–0 to Celtic.

Chisholm started his career at Sunderland where he spent seven years and was a member of the side that reached the final of the Football League Cup in March 1985, where they lost 1–0 to Norwich City.

[2] This meant that Chisholm achieved the unusual feat of playing in League Cup Finals in the same calendar year in both England and Scotland.

[2] Chisholm had assistant manager roles at Partick Thistle, Clydebank, Ross County, Airdrie, Falkirk and Dundee United, primarily working with Ian McCall.

Chisholm's team then retained SPL status in dramatic style with a late Barry Robson penalty at Inverness on the final day of the season.

Despite spending considerable money on players such as Lee Miller, Dundee United were eliminated in the qualifying stage of the UEFA Cup by Finnish team MyPa.

In March 2008, Chisholm guided Queens to only their second ever Scottish Cup semi-final appearance with a 2–0 quarter final victory against Dundee, a game notable for a goal from 84 yards by Ryan McCann.

Chisholm made the following comments after leaving QoS:[11] I had an excellent working relationship with Chairman Davie Rae, a person I always had a tremendous respect for.

I'll always remember the great support shown by Queens' fans over the past two and a half years and the players themselves have been fantastic and a pleasure to work with.

And I genuinely mean that!Chisholm took the Dundee job while they were top of the First Division, although the club had just sacked Jocky Scott after going four games without a win.

[12] Chisholm said ahead of his first game in charge, "It was an opportunity I just couldn't pass by at my time of life, but it will be a strange experience being on opposite sides tomorrow night."

[13] After leaving Dundee in October 2010 and spending over a year out of professional football, Chisholm set up an estate agent business with his wife.

[14] He resigned from his position at East Fife in October 2012 due to the pressures of combining both tasks and commuting from Lenzie to Methil.