City stunned the eight-time Cup champions 26 years ago in one of the most memorable finals in this illustrious competition, but the Midlanders have fallen a long way since that day.
Mark Robins' npower League One side sat 52 places below the Londoners in the league ladder this morning and that much was evident in the opening stages as Tottenham controlled the game before taking the lead through Clint Dempsey.
The American's deflected shot flew into the path of the excellent Gareth Bale, who made it 2-0, and the Welshman returned the favour soon after, setting the American up to make it 3-0 just before half-time.
Coventry barely got a sniff of goal all afternoon and the game could have turned in to a real hiding had Dempsey, Emmanuel Adebayor and Steven Caulker taken further chances.
Tottenham controlled the game from the off and were in front after 13 minutes. Bale flicked on Gylfi Sigurdsson's pin-point cross and Dempsey nipped in front of his marker to stab the ball past Joe Murphy.
Only a crucial tackle from Richard Wood prevented Dempsey from adding a second four minutes later. Wood put in a block to deny Dempsey and the American was thwarted again moments later - this time by Adebayor, who could not get out of the way of the forward's powerful shot as it made its way in to the far corner.
With 32 minutes gone Dempsey had another shot blocked by Wood, but this time the ball flew to the back post where Bale turned the ball in from close range past a stranded Murphy.
Five minutes later Bale powered a long cross to the back post where Dempsey steered a pinpoint header over two Coventry defenders on the far post to make it 3-0.
The Sky Blues then had a glorious opportunity to pull one back with their first chance of the match, but Kyle Naughton nicked the ball off Franck Moussa's feet just before the striker could shoot from 10 yards out.