McLean spent 21 years as manager of Dundee United until his retirement in 1993, becoming the club's longest serving manager. At that point, the club had had only two managers in a 34-year period, but since then have had a much higher turnover. Tam Courts, appointed in 2021, is the club's eighteenth manager or head coach in the 28 years since McLean. Up until 2000, McLean himself had chosen his successors, having become club chairman in 1988 and initially combining this role with that of manager, a unique situation in Scottish football. His immediate successor, Ivan Golac, won the previously elusive Scottish Cup in 1994, but he left the club the following year shortly before United were relegated after 35 years in the top flight. Promotion back to the Premier Division was won under Billy Kirkwood, who was followed as manager by Tommy McLean, the chairman's brother. Dundee United won the Scottish Cup for a second time in 2010, under Peter Houston. Other managers to have taken the club to major cup finals are Tommy McLean, Gordon Chisholm, Craig Levein and Jackie McNamara.