The countdown of Chelsea’s 50 greatest players continues this week with a few throwbacks to a time where the club wasn’t fighting for the title each season and every minute of European football was cherished. Three of the five names that feature this week went on to either manage or coach Chelsea after, or in one case before, retiring.

30. Roberto Di Matteo

The Italian is known for two things he did during his time at the club; he was the man who brought the holy grail of the Champions League back to West London but his strike in the 1997 FA Cup Final will go down as a highlight in his playing days. Just 42 seconds into the game at Wembley, Di Matteo launched an unstoppable strike over the Middlesbrough keeper and off the underside of the bar. It stood as the quickest FA Cup Final goal at Wembley for over a decade but his place in history has been cemented because of it. The Italian went on to win another FA Cup (scoring the winner in the final against Aston Villa in 2000), a League Cup and a Cup Winners’ Cup in the final years of his career at Stamford Bridge. The Italian donned the number 16 shirt for the Blues for 6 years but it was at the age of 31 when he was forced to retire because of a serious leg injury that he couldn’t recover from. He eventually turned to coaching and the rest is history.

29. Ray Wilkins

One of our own. Wilkins was brought through into the first team at the age of just 17 in 1973 and it wasn’t long before he became one of the most influential players at the club. He captained the side during his late teens and led the young side to promotion to the top division and the club managed to stay there the following season. His performances didn’t go unnoticed and played for England on numerous occasions during his time at the club. The midfielder won the Player of the Year at Chelsea for two consecutive seasons in the mid-1970s. He was sold to Manchester United in the midst of a financial crisis at the club with Chelsea needing to clear some debts and the £800,000 fee that they received for Wilkins would’ve helped a lot.

28. Branislav Ivanovic

Perhaps Chelsea’s greatest ever right back and was a key part of the club during its most successful era. The Serbian joined Chelsea in 2008 from Lokomotiv Moscow as a centre-back but his attacking threat down the right side was a key part to his game and he soon became a stalwart on the right of defence. Ivanovic scored a number of important goals including a brace at Anfield, an extra time winner against Napoli and a stoppage-time trophy clincher against Benfica. Along with Didier Drogba, he can be considered the most reliable big-game player in the club’s recent history because of his contribution on the highest stage. His medal collection includes those from 3 Premier League triumphs, a Champions League victory and numerous Wembley wins. Not to mention places in 2 PFA Team of the Years and a Champions League Team of the Year as well as being names Serbian Player of the Year twice during his successful time at the club. A true modern great despite his loss in form towards the end of his Chelsea career.

27. Glenn Hoddle

The fact that Hoddle has made this list despite spending just 2 seasons as part of the playing squad says it all. His class and ability shone through during the last 2 years of his career at Stamford Bridge but success in the form of silverware evaded him. An FA Cup runners-up medal is all his has to show for his Chelsea career both as a player and a manager. He often played as a sweeper in a back 3, way before Antonio Conte’s time, and was, more often than not, the outstanding player in the team. Despite having a bare trophy cabinet, Hoddle managed to attract a couple of world-class players to the club to kick-start the successful era we’ve been enjoying for around two decades, such as Ruud Gullit and Gianluca Vialli. His influence on the club and the way things are run nowadays cannot be underestimated and his time as a player is fondly remembered by all.

26. Terry Venables

Like Ray Wilkins, Venables started his career at Chelsea and quickly became a huge success at the club. The hype surrounding the youngster began before he even made his senior debut for the club after impressing in the FA Youth Cup. Venables went on to play almost 250 games for the club and was an integral part of the side that gained promotion to the first division in the 1960s, scoring 31 goals in total from midfield. He scored a penalty in the first leg of the 1965 League Cup final that the Blues went on to go and win against Leicester by the single goal and he lifted the trophy as captain. He had his fair share of problems with the manager, Tommy Docherty, during his time at the club and, having done his coaching badges at the age of 24, had differing tactical views. Venables went on to become a hugely successful manager and that is partly due to what he experienced during the first years of his career at Chelsea.