The former England Captain was speaking on Up-Front with Simon Jordan.
Despite having an illustrious career consisting of five Premier League titles, five FA Cups, three League Cups, one UEFA Europa League and one UEFA Champions League title Terry admitted it was his failures that still haunt him.
Manchester United fans will look back fondly on that rainy night in Moscow in 2008, which saw them secure their third European triumph and second under Sir Alex Ferguson.
However, Terry slipped in the run-up to the decisive penalty, an act that he still thinks about to this day.
The Englishman went on to secure Champions League Silverware four years later but was banned for the final against Bayern Munich. Didier Drogba and Petr Cech starred that day, in a historic penalty shootout victory.
“The worst moment in my footballing career for sure. Still not over it today; don’t think I ever will be. It’s interesting because as a player you have so many highs… it’s the ones you miss out on (that stay with you).
“That night we lose (2008 Champions League Final) and go back to the hotel. The manager demands everyone downstairs for a drink. I can’t go downstairs and face the lads, I’m in my room. Eventually, I go down and have a beer with the group.
“I just remember standing looking over Moscow in my hotel. Just looking out… just asking, ‘Why? Why then? Why did it start raining? Why did I slip?’
“Probably the hardest thing was that three days later, we met up with England; we had a friendly at Wembley against the USA. We drew the game one all and I ended up scoring a header from outside the box; that was probably the hardest moment. If I could swap any goal in my career it would be that.
“I scored a header from 18 yards (out) and after the game, it broke me; I was bad. People are more open with this stuff now; I was going through emotions that probably a lot of people speak about today but you have to bottle it… and move on.”
Terry has flirted with coaching picking up the Aston Villa assistant manager role in recent years but revealed he is working with Chelsea’s youth ranks as they are ‘on his doorstep’ admitting he still loves the Blues.
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