Maddison, who limped off in the defeat at the Tottenham Hotspur Stadium, commented on an Instagram post of Terry celebrating his old side's win.
The Chelsea legend shared a video to his nine million Instagram followers showing him and wife Toni dancing on a bar.
He wrote alongside the video: "When Chelsea beat Spurs 4-1 on a school night and the tequila comes out, and you end up dancing and singing on the bar."
Maddison responded saying: "Jesus, u have ur eyes closed when it was 11 v 11 first 15 JT?"
Terry replied: "Madders, don't worry mate you will get used to it."
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During Terry's era at Chelsea, the club enjoyed plenty of success at their rivals. Even giving their stadium the mocking nickname 'Three Point Lane'.
Spurs' unbeaten start to the season came to an end in dramatic fashion against their rivals on Monday.
Even though the Blues won 4-1 they did not come out of the game with a huge amount of credit.
Jason Cundy bursts into talkSPORT studio to mock Jamie O'Hara following Chelsea's win at Tottenham
Spurs played the last 35 minutes with nine men, with five goals disallowed across the whole match.
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They also lost Micky van de Ven, as well as Maddison, to injury in the first half.