Most expensive players by age 39 years old: Craig Brewster, Inverness – Dundee Utd, 2006. £340k.

This is possibly the only instance of humble Dundee United featuring on a list of the most expensive transfers in football. Craig Brewster returned to the club as player-manager in January 2006, although the move wasn’t a successful one. The Tangerines went unbeaten for their first three matches, but then went on to win only one match for the remainder of the season. Brewster would cling on until October.

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