21. Ralph Milne

Signed from: Bristol City (£175,000), November 1988
Debut: 2-2 draw vs Southampton, November 19th 1988
League Record: 19 games (+4 as sub), 3 goals
Sold to: Sing Tao of Hong Kong (free transfer), summer of 1991

Often brought up in "Worst United Player" polls, Ralph Milne was a gamble by Fergie to fill the left-wing space until Lee Sharpe was ready. It didn't work, but the small fee perhaps warranted the risk.

After all, at his peak, Milne was part of a Dundee United team that won the Scottish championship and were becoming a force in European football. In his best years, he was scoring for fun in domestic and continental competitions and to this day is highly rated by fans in that part of Scotland.

It all went downhill fast though, for whatever reasons and his powers were well on the wane by 1988. Indeed, we signed him from Bristol City, who were then in the third tier of English football. He'd come to England to sign for Charlton but his form for them had caused the drop down. Fergie obviously remembered Ralphie from his glory days and after flogging Jesper Olsen, needed a replacement.

United fans, understandably, were underwhelmed. Used to erratic but talented wingers like the Dane and Gordon Hill, the slower style of Milne was never going to go down well. He had the odd moment, but wasn't able to inspire a struggling team and after the end of the 1988/89 season, he made only one appearance off the bench the next year, spending the best part of two campaigns dossing round the reserves, with the exception of a short spell on loan down at West Ham.

Fergie reckons Milne couldn't handle the sheer pressure of playing for United, which may be true, but he perhaps should have judged that Milne wasn't a big club man. After he left, according to Lee Sharpe, he sold a story to the tabloids about players getting off their kites in Amsterdam during our trip over to Holland for the European Cup Winners Cup final in 1991 - thanks for that Ralphie!