28. Mike Phelan

Signed from: Norwich City (£750,000), July 1989
Debut: 4-1 win vs Arsenal, August 19th 1989
League Record: 88 games (+14 as sub), 2 goals
Sold to: West Bromwich Albion (free transfer) May 1994

Into a new season, then. Following a 1988/89 season that defined "mediocre", Fergie brought out the chequebook to bring five new names to the club. Of which the first one we'll come across is Mike Phelan. He was an odd signing on some levels, paying a fair sum of money for a player who was hardly dynamic even in his best years at Norwich. Essentially, I think we were buying a younger version of Mike Duxbury. 

For his first two seasons, Phelan mainly played in a midfield that was often lop-sided due to our lack of a right winger, a job which would sometimes fall to Mike, which seems laughable in hindsight, given he had a chronic lack of pace. I can only assume there was nobody else to do the job after we’d flogged Gordon Strachan and Fergie lost faith with Russell Beardsmore. Mercifully, the emergence of Lee Sharpe meant most of the play went down the other flank. That said, it was our man here who set up Mark Robins to score the memorable winner in the 1990 FA Cup semi-final. Phelan wasn’t a terrible player, and often did his job competently enough, but the feeling was that he wasn’t going to play a big part in winning the big prizes. 

With subsequent signings of other players and the appearance of some kid from Salford, he ended up spending the next two seasons as a classic utility player, often filling in at right back. In our first Premiership winning campaign, he just played enough games for a medal, and even scored his first ever goal at OT during a FA cup game vs Bury, but barely featured the next season and was binned off to WBA on a free. 

As a player, he was solid enough but never the kind of quality that wins leagues – for one thing, he never scored anywhere near enough. He also had a moustache, and I have a problem taking footballers with muzzies seriously. On the plus side, he had an ace chant to the tune of the Righteous Brothers’ classic: “You’ve lost your hairline, Phelan...” 

For several years, he worked back at United as an assistant manager and the target of no shortage of ire from some sections of the support, as well as being the source of much amusement for his taste in training shorts.