Terry Venables

After winning back-to-back FA Youth Cups with Chelsea in 1960 and 1961, Venables became the midfield general and leader of our youthful side under Tommy Docherty and was at the forefront of the club’s first big cup success against Leicester City in the 1965 League Cup final. El Tel got on the scoresheet in the first leg as he converted a penalty in a 3-2 home win and then helped ‘Docherty’s Diamonds’ frustrate the Foxes in a 0-0 draw in the return game at Filbert Street as we brought the three-handled trophy back to Stamford Bridge for the first time.

Ron Harris

Harris took over the captaincy when Venables left in 1966 and the skilful but tough and uncompromising defender played a key role in our first FA Cup success in 1970. ‘Chopper’ set up Ian Hutchinson’s late equaliser in a 2-2 draw with Leeds United at Wembley before effectively shackling dangerman Eddie Gray in a 2-1 victory in the replay. He also skippered the side to our first European title a year later as we outlasted Real Madrid to win the Cup Winners’ Cup after another replayed final but missed out on a third trophy in three years when we were beaten by Stoke City in the 1972 League Cup final.

Dennis Wise

An FA Cup winner with Wimbledon in 1988, Wise moved north of the Thames two years later and enjoyed a fruitful 11-season spell at the Bridge which culminated in him lifting five trophies in four seasons from 1997 to 2000 as he captained us to victory in two FA Cups, the League Cup, Cup Winners’ Cup and Super Cup. The feisty and combative midfielder often bossed proceedings in the middle of the pitch for the Blues and was named Man of the Match in our 1998 League Cup and 2000 FA Cup triumphs.

John Terry

Chelsea’s most successful captain enjoyed plenty of domestic cup success to go along with his five Premier League titles as he led us to four FA Cups and three League Cups during his time as skipper of the Blues. While there were several excellent performances from our Captain, Leader and Legend in all of those finals , his stand-out displays came in the League Cup in 2005 and 2015 as he was named Man of the Match in both games and scored the decisive opening goal in our victory over Tottenham Hotspur in the latter.

Frank Lampard

As the club’s vice-captain for 10 seasons, Lampard lifted several trophies alongside Terry and deputised for him as our leader on the pitch on a number of occasions. He took over the armband in our 2007 League Cup final triumph against Arsenal when Terry was knocked out by an accidental kick to the head and also captained the team in the Champions League final against Bayern Munich in 2012 and Europa League final against Benfica a year later when our regular skipper was unavailable due to suspension or injury.

Gary Cahill

Cahill was named club captain when Terry left the club in 2017 and the long-serving centre-back got the opportunity to hoist some silverware at the end of that campaign after he helped shut out Manchester United 1-0 in the FA Cup final. While his playing time was significantly reduced under Maurizio Sarri the following season, he rounded off his time with the Blues by lifting the Europa League with Cesar Azpilicueta after our 4-1 thumping of Arsenal in Baku.

Cesar Azpilicueta

After filling in for Cahill as our leader on the pitch for most of 2018/19, Azpi took over as club captain in 2019 but missed out on glory that season as we were beaten by Arsenal in the FA Cup final. However, he more than made up for that in the campaign that followed as the Blues conquered Europe for a second time with a 1-0 victory over Manchester City in the Champions League final before we also secured the Super Cup by downing Villarreal in a dramatic penalty shoot-out.