Best Chelsea Players to Ever Wear the Number 16 Jersey

Roberto Di Matteo

Not only is the manager who delivered the Champions League, Roberto Di Matteo was a star on the pitch for the Blues in the 90s. He was one of their many exciting attacking signings who helped them rise through the ranks in the decade to become one of the Premier League’s major players by the time Roman Abramovich came along to buy the club.

He played in midfield, where his passing and shooting range made him a consistent threat. His career was sadly cut short from injury, but he accumulated 39 goal contributions in 175 appearances for the team. During that time he won the FA Cup, League Cup, UEFA Cup Winners’ Cup, and the UEFA Super Cup.

David Rocastle

A man who built his legacy with Arsenal, David Rocastle was an England international with the technical abilities to play across the midfield and even as a winger. Knee injuries saw him cycle through teams after the Gunners cut their ties with him and he eventually landed in London once again as he joined Chelsea in 1994.

The Blues spent a million pounds on Rocastle despite his well-documented knee injuries, believing it to be better to have him on the field at all than to not have him. He was carefully managed by Glenn Hoddle, often being subbed off in starts. His one season of health showcased his talent, his ability with the ball and experience of winning titles with Arsenal made him a pivotal part of that 1994/95 campaign.

He sadly would only play once more after that term, injuries cropping up again before he was sent on loan a number of times. Rocastle is potentially one of the most unlucky players in history. Started his career needing contact lenses, plagued with knee injuries in his prime, before succumbing to illness just two years after his retirement.

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