Late goals from Djed Spence and Brennan Johnson secured Tottenham an undeserved 2-1 victory at Coventry in the League Cup third-round.
It appeared Brandon Thomas Asante's second-half strike would add more misery to Spurs' start to the season when he gave the Sky Blues the lead their play warrented.
In the final ten minutes, Spurs desperately looked for an equaliser and it finally came when Dejan Kulusevski's through-ball was poked home by Spence two minutes from time.
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Then two minutes into injury time, former Coventry man James Maddison's fine through-ball was classily clipped home by Johnson.
Ange Postecoglou reminded reporters that he always wins a trophy in his second season last week and now their fans will wonder if this late escape will be the precursor to them winning this Cup, with the last time they lifted silverware coming in 2008.
Talking Point - Name...on...the...trophy?
Just short of 34 years after Mark Robins' goal extended Sir Alex Ferguson's time at Old Trafford leading to the unprecedented domestic success to follow over the next two decades. Could United's hero that day at the City Ground have witnessed from the oppostion dug-out Ange Postecoglou's pivotal moment at Tottenham?
There is a fair way to go. Four ties, likely including two against teams higher than them in the Premier League, but this felt like a match with some providence attached.
Postecoglou needlessly, and probably inadvertently, put pressure on himself when he made the comment about his incredible success in his second season at clubs.
After their slow start to the Premier League, which has seen them take just four points from as many games, the team playing so poorly in the East Midlands and continuing to showcase the toothless forward play which has been evident in three of their four league games this season, would have increased the noise from those questioning the Australian supremo.
Two attacking moves with high quality, unsurprisingly both involving Maddison, turned things around for Tottenham and will have the Spurs fans pondering another Aussie's Dream.
Player of the Match - Jack Rudoni (Coventry)
All of City's forward line looked impressive as they imposed themselves on Spurs for most the of the match, but Rudoni was the impetus behind most of their attacking moves.
The £5.3 million signing from Huddersfield has the quality to play in the top flight and if he can reproduce this form consistently he may guide Coventry to these heights once more.
Player Ratings
Coventry: Wilson 7; Van Ewijk 6, Thomas 6, Binks 7, Bidwell 6; Eccles 7, Allen 7, Rudoni 8*; Thomas-Asante 7, Bassette 7, Wright 7. Subs: Simms 6, Sheaf 6, Mason-Clark 6, Torp 5,
Tottenham: Forster 6; Gray 6, Dragusin 6, Davies 7, Udogie 6; Bentancur 6, Sarr 6, Bergvall 6; Odobert 6, Timo Werner 5; Solanke 6. Subs: Johnson 7, Son 6, Maddison 7, Spence 7, Kulusevski 7.
Match Highlights
Key Stat
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