Gary Cahill proved himself against quality strikers at Chelsea, but one particular test against Harry Kane sparked concern for Jose Mourinho.
The Blues faced Tottenham in the 2015 League Cup final two months after they were beaten 5-3 by their London rivals at White Hart Lane.
Kane scored two goals against a Chelsea defence that had Cahill and John Terry as the centre-backs in what was just one of their three league defeats of the season.
Mourinho knew his trusted defensive duo would be desperate to put in improved performances in the Capital One Cup final at Wembley.
After all, Cahill was able to keep other top strikers quiet prior to the match, such as Wayne Rooney, Sergio Aguero and Romelu Lukaku.
However, Mourinho appeared keen to ask the defender if would be up to scratch for another tough test against Spurs star Kane.
Speaking on John Obi Mikel's The Obi One Podcast, Cahill said: "One time, I don't think you would have known this John, when we were playing Tottenham in the League Cup [final] and I think a few weeks before that we played them away from home.
"I think Harry Kane scored two or three goals, like we got beat, which is rare against Tottenham, I think it was five, whatever. He pulled me in and he was saying, 'Are you alright? Are you alright for the final?'
"And I was thinking, 'What?' He was like, 'But Harry Kane scored', two or three goals or whatever it was, I can't remember now, but like, 'Has that affected you?'
"Almost questioned like I was staying up every night worrying, thinking about that, thinking, 'Oh, I've got the final coming, he's going to teat me apart.'"
Those fears proved to not be an issue as they went on to win the final 2-0.
Earlier in the podcast, Cahill spoke on Mourinho's mind games when commenting on an incident that saw the legendary boss threaten to sign Raphael Varane and another defender to replace him and Terry.
Following on from that, he added: "But that was just one moment of what I was touching on then, the kind of mind games that he played, and also I'd imagine he wouldn't do that to some other players.
"So when he was asking me that question, again, I could just feel like a spider coming up my back thinking, 'Are you questioning... you think I'm worried about...?' I was like, 'Please play me, play me in the game.'
"I came out thinking, 'I can't believe he's questioning my character there', like he was thinking I'm going to s*** myself against Kane, I was fuming.
"Look back now, [genius] yeah yeah, I could just imagine him as I went out going [whilst rubbing his hands], 'Lovely, got him right where I want him there.'
"He [Kane] started, we won 2-0, [he] didn't score, but I still came off, even after the game thinking, 'I knew I'd do it!' He's probably just thinking, '[I got] exactly what I wanted from you.'"
Mourinho showcased his trust in Cahill by starting him in the League Cup final against Spurs, a decision that proved successful as Chelsea won 2-0 thanks to goals from Terry and Diego Costa.
Kane, who scored an incredible 31 goals in all competitions during the 2014/15 season, was unable to add to his tally against the Blues.
Chelsea also went on to win the Premier League title two months later, with Cahill playing in all but two of their 38 matches across their triumphant campaign.