Coventry 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.
Indeed the only thing the 5,000 travelling fans had to be cheerful about was the half-time appearance of Gary Mabbutt, the man who scored the own goal that gave the Midlanders their famous Cup win 26 years ago.
The game proved to be a good run-out for Tottenham's squad players, plus Benoit Assou-Ekotto and Scott Parker, who were both making their return from long-term injuries.
Parker, who faces a fight to get back in to Tottenham's first team, gave manager Andre Villas-Boas an early reminder of his talents, breaking Coventry's midfield up with a couple of crunching tackles.
Tottenham controlled the game from the off but Coventry initially rode out the pressure. Parker and Tom Huddlestone both had wayward shots, but there was nothing amiss about Dempsey's effort on goal 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.
Bale looked fresh and determined to make an impact after missing Spurs' last game through suspension. The Welshman tore down the left flank from the halfway line, beating five players before angling a shot across Murphy that crept a couple of inches wide.
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.
Dempsey, looking to complete a first-half hat-trick, took down the ball on his thigh in injury-time, whipped the ball over his head and fired a peach of a volley just over the bar.
Spurs continued to dominate after the break. William Edjenguele shrugged Adebayor off the ball in the Coventry box but referee Michael Naylor waved the Togolese's protests away.
Huddlestone provided Caulker with an easy opportunity to make it 4-0 but the defender headed a perfect cross wide.
Huddlestone gave the ball away in his own half, allowing Leon Clarke to drive at goal, but Caulker came to the rescue before Conor Thomas could pull the trigger.
Only a reflex save from Brad Friedel denied Edjenguele a consolation goal as Coventry grew in confidence.
Clarke arrived just too late to latch on to Gary McSheffrey's cross with 11 minutes left.
Spurs came back in to the game in the final 10 minutes. Andros Townsend went close to scoring on two occasions following his introduction from the bench while Edjenguele's handball in his own box went unpunished.
Coventry had the ball in the net through McSheffrey in injury time, but the goal was ruled out for offside.
- Sports & Recreation
- Clint Dempsey
- Gareth Bale