Sinclair started his career at Stamford Bridge in 1990, going on to appear over 200 times for the Blues, winning the 1997 FA Cup and the 1998 League Cup.
A Jamaican international, he stayed with his first team until 1998, before moving on to a number of other sides, signing with Colwyn Bay in 2012, becoming their player-manager in February 2013.
He leads his side out in the FA Cup this weekend, with a third qualifying round replay at Warrington Town moving the non-leaguers one step closer to the tournament proper, and four victories away from a potential third round tie against one of the English footballing giants.
The 42-year-old said: “I would be crazy if didn’t think about playing Chelsea.
“Football is about dreams – as a player and as a manager. I want to manage at a high level against the best so it would be incredible to play Chelsea or another one of the big clubs.
“But that’s wildest dreams stuff so we have to be realistic and keep thinking about where we are. Each round is more money which would be huge for the club.”
Having won the 1997 FA Cup with the Blues, the trophy that kick started the current era of success at Stamford Bridge, Sinclair revealed what then-head coach Ruud Gullit did to motivate the first-team squad - something he certainly will not be doing with his current side.
“Ruud gave us sip of champagne.
“Ruud did things like that. It got the players relaxed and helped our mindset.
“It’s certainly not going to be happening here. The budget doesn’t stretch to that.”