Andy Cole for Keith Gillespie
In January 1995, Newcastle lost their key striker as Andy (or Andrew, depending on your preference) Cole was sold to Manchester United in exchange for £7 million and Northern Irish winger Keith Gillespie.
Such a move seemed to take the North East by surprise, with Cole having established a very promising reputation in front of goal at St. James' Park after joining from Football League outfit Bristol City.
WINNERS - MANCHESTER UNITED
No contest here, I'm afraid. Cole, who eventually retired from the game in 2008 after further spells with the likes of Blackburn, Fulham and Portsmouth, was a monumental success at Old Trafford - striking a fearsome partnership with Dwight Yorke as Manchester United dominated English football in the late 90s under Sir Alex Ferguson.
While Gillespie made over 100 appearances for the Toon in a three-year stint at the club, Cole was undoubtedly and unsurprisingly the better signing. Five Premier League titles, two FA Cups and a Champions League trophy are testimony to that.