The winger won two Premier League titles with the club
The most successful period of Damien Duff's club career came at Chelsea.
One of the first signings of the Roman Abramovich-era, the Dubliner ended up winning two Premier League titles and a League Cup under Jose Mourinho.
Duff spent three seasons at Chelsea, before a big-money move to Newcastle. Speaking to FourFourTwo, Duff admits there were telltale signs on front of him that he shouldn't have moved north.
"I cried on the day that I left – looking back, that probably should have told me I was making the wrong call, as I never cried when I left Blackburn, Newcastle or Fulham, or even when I retired. But it was my own decision."
"I had friends at Newcastle – Scott Parker, Shay Given – and I wanted to give that a real go, but I had a disaster. I gave them everything but sometimes moves don't work out."
Although the move from Blackburn Rovers to Chelsea was the biggest of his career, Duff revealed he had opportunities to join Liverpool. One of those came when he was still at Blackburn.
"I came close [to joining Liverpool] two or three times," he revealed. "The first was a year or two before I signed for Chelsea. I would have gone there, but Blackburn wanted a big fee so not too many clubs could afford to buy me back then! Then when I was leaving Chelsea, the same move nearly happened again."
Duff's move to Anfield never materialised, but after a testing spell at Newcastle, he enjoyed a late career resurgence with Fulham. Duff was part of the team that reached the Europa League Final in 2010.
100 caps for Ireland and two Premier League titles, means Duff can have few regrets with his career, but that move to Newcastle will live long in the memory.