The 44-year-old lifted five Premier League titles, four FA Cups and one Champions League among other trophies with the West London club who hold a special place in his heart, even after retirement.
Terry wants to return to the dugout at Stamford Bridge and recently admitted that it is his dream to manage the side but admitted that it would probably never happen as he fails to land lesser jobs as he searches for a head coach role.
"I'm not sure it ever happens, to be honest. It's my one last dream I have at the football club. I've done everything at Chelsea. And for me now, the one thing that is missing is being the manager of the football club.
"That's why I went into coaching when I finished playing. My idea and dream was to learn my trade a bit. As a player, you retire after 22 years… Listen, 100 per cent, you learn enough to go into management.
"The level I played at and the managers I played under. But it doesn't give you the right you go into management at a certain level. You still have to learn and understand what it takes."
Terry’s former England teammates Steven Gerrard and Wayne Rooney and Frank Lampard have all had managerial stints at the likes of Coventry, Rangers and Birmingham.
He admits that if he were to get back into coaching, it would be at a much lower level compared to the Premier League, which would be a stretch for his low experience.
"I'm not saying a job in the Premier League or the Championship - but a job at League One level.
"I didn't even get a sniff. I had interviews and it was just "you have no experience". When I see some people managing today, it baffles me, it really does.
"In terms of 'am I frustrated', yes, absolutely, because I have a lot of good attributes to be a really good coach or a really good manager but, unfortunately, that's not happened."