Late goals by Djed Spence and Brennan Johnson helped Tottenham avoid an almighty upset at Coventry in the Carabao Cup.
Spurs were set to follow up Sunday’s painful derby defeat to Arsenal with a 1-0 loss in the third round after Brandon Thomas-Asante fired the Championship side into a deserved lead after 63 minutes.
Moments earlier, Ange Postecoglou’s decision to substitute Lucas Bergvall had been met with boos from the away end.
However, with time running out and Postecoglou’s bold prediction last weekend of always winning silverware in his second season being set to come back to bite him, Djed Spence found an equaliser with three minutes left.
Spot-kicks were still on the cards until Rodrigo Bentancur played through Brennan Johnson, who chipped home in the 92nd minute to earn Tottenham a precious 2-1 win and leave their travelling support singing about Wembley.
This was the first meeting between the clubs in 11 years, but it was a fixture synonymous with the 1987 FA Cup final when Coventry triumphed 3-2 to clinch the only major trophy of their history.
Postecoglou was eager to deliver silverware for Spurs, but made eight changes from Sunday’s north London derby loss.
Fraser Forster was recalled for his first start in more than 12 months and almost gave away a goal inside 60 seconds, but atoned for a poor pass out from the back with a fine save to deny Jack Rudoni from 20 yards.
When Tottenham did eventually settle, they were forced into a 17th-minute substitution when Wilson Odobert went down after a strong challenge from Jake Bidwell.
Johnson was sent on and while the visitors continued to dominate possession, they could not fashion any chances and almost conceded again during an end-to-end 38th minute.
Firstly, Rudoni’s shot from Bidwell’s cross was blocked by Destiny Udogie and Johnson led the Spurs counter-attack but his cutback failed to pick out a team-mate, which resulted in Norman Bassette being sent away only to fire over.
After no first-half shots and a smattering of boos from the away crowd, Postecoglou sent on full-back Spence and two minutes later they did register an effort of note.
Dominic Solanke carried the ball and found Johnson, but his low effort was blocked by ex-Tottenham youngster Luis Binks.
It was not a sign of things to come as after Timo Werner was again dispossessed, Bassette tested Forster with a low strike.
The 24,606-strong crowd could smell blood and wanted a penalty after 56 minutes when Bidwell raced onto Ben Wilson’s pass and collided with Forster, but play continued and Spurs’ stand-in captain Ben Davies slid in to deny Haji Wright’s goalbound effort.
Thomas-Asante lifted over shortly afterwards before Postecoglou’s night went from bad to worse as his decision to bring off the lively Bergvall sparked boos.
Seconds later and the home faithful were on their feet in celebration after Bassette produced a superb cross for Thomas-Asante to slot past Forster.
No immediate reaction was evident as Ellis Simms headed wide soon after for Coventry.
James Maddison did go close in the 77th minute when he controlled Radu Dragusin’s long-range pass but curled wide from range before Ephron Mason-Clark failed to sufficiently connect with Simms’ deflected shot.
As Postecoglou was facing up to a second consecutive early exit in this competition, his blushes were spared when Dejan Kulusevski linked up with Spence, who prodded home for his first Spurs goal.
With three minutes left, Tottenham sensed their moment and in the second minute of stoppage time Bentancur played in Johnson, who rolled the ball past Wilson to ensure the full-time whistle was greeted with chants of ‘Wembley’ from Tottenham’s travelling support.