Tottenham were sent tumbling out of the FA Cup by Middlesbrough as Josh Coburn's 106th minute strike condemned Antonio Conte's side to a 1-0 extra time defeat at the Riverside Stadium.
From the outset it was evident Spurs were willing to allow Middlesbrough to control possession to open up space going in the opposite direction.
Dejan Kulusevski, who has taken to life at Tottenham very well so far, manoeuvred his way into the Boro penalty box and looked set to pull the trigger from point-blank range early on. However, Dael Fry recovered smartly to deny the former Juventus man with an expert sliding challenge.
Spurs' threat on the counter-attack was laid bare with perhaps the best opportunity of the opening half in the 38th minute. Matt Doherty was released into space down the right hand side when Boro goalkeeper Joe Lumley rushed out of his goal. The former Wolves man skipped over the challenge but, with the goal gaping from range, he badly miscued his finish.
However, the best chance of the game belonged to Middlesbrough from a corner shortly after the interval.
Jonny Howson's delivery was met by Matt Crooks, unmarked and from five yards out, but the midfielder steered his header over to the dismay of the home support.
Harry Kane then had the ball in the net from a corner after Eric Dier had previously worked Lumley from a free-kick, but the linesman raised his offside flag to curb the Spurs celebrations.
Howson nearly caught out Hugo Lloris at his near post from a free-kick routine involving Marcus Tavernier in the 64th minute, but his effort flew wide.
Folarin Balogun then got on the end of a flowing Boro move ten minutes from time, but the on-loan Arsenal man was leaning back when he unleashed his finish from inside the penalty area.
Antonio Conte responded to Middlesbrough's superiority by calling on Steven Bergwijn from the bench and the Dutchman almost made an immediate impact when he burst into the penalty area. Just as he was about to pull the trigger, however, Paddy McNair flew across to thwart the danger.
Middlesbrough ought to have won it with a string of opportunities in the final minutes of normal time. First, Lloris got down expertly to deny Isaiah Jones after the winger was released inside the penalty area by Tavernier, before Howson met the resulting corner in space but could only divert his header wide.
Son had a couple of opportunities either side of the full time whistle to break the deadlock, before Lloris was called into action when Tavernier met Jones' cross with a side-foot volley at the far post 14 minutes into extra time.
Middlesbrough's endeavour was eventually rewarded just a minute into the second half of extra time. Substitute Coburn latched onto Howson's smart through ball before composing himself to thump his finish into the far corner beyond Lloris.
Conte cut a dejected figure on the sideline as Spurs failed to muster a response, extending their misery in cup competitions in recent years.
Here's how Tottenham rated on the evening.
Tottenham player ratings
1. Goalkeeper & defenders
Hugo Lloris (GK) - 5/10 - Had very little to contend with amid a spate of missed chances for Boro and could do little to prevent a thumping finish from Coburn.
Cristian Romero (CB) - 6/10 - Made a couple of vital last-ditch blocks, commanding his penalty area very well. Got involved in minor scuffles a bit too often.
Eric Dier (CB) - 5/10 - Often looked to spring Spurs forward with long passes out of defence.
Ben Davies (CB) - 5/10 - Defended resolutely, although he didn't have many opportunities to step into midfield with the ball.
2. Wing-backs & midfielders
Matt Doherty (RWB) - 4/10 - Broke into some promising areas, but his touch and/or final pass invariably let him down.
Harry Winks (CM) - 3/10 - Wasn't penetrative enough with his passing, fading out of the game for long periods.
Pierre-Emile Hojbjerg (CM) - 5/10 - Always ambitious in his passing, constantly looking to fire passes into Kane to spring Spurs forward. A rare bright spark.
Ryan Sessegnon (LWB) - 3/10 - Made a couple of smart runs in behind during the early exchanges, but he seemed to get disillusioned as the game wore on.
Dejan Kulusevski (RW) - 7/10 - Spurs' brightest attacker, constantly looking to supply Kane and run beyond the Boro backline.
Harry Kane (ST) - 3/10 - Very effective at dropping deep to launch Tottenham counter-attacks early in the game, but he couldn't impact the game in the penalty box.
Heung-min Son (LW) - 2/10 - Couldn't really stretch his legs in behind the Boro defence and, whenever he received the ball, he was usually wasteful.
Steven Bergwijn (LW) - 6/10 - Added an extra dimension to Spurs attack when he was introduced.
Emerson Royal (RB) - 1/10 - Barely had an effect on the game as Conte moved to a back four, and was playing Coburn onside for Boro's goal. Tragic.
Sergio Reguilon (LWB) - N/A
Dane Scarlett (ST) - N/A