So here's the updated news about 2021–22 FA Cup. Antonio Conte began to resemble a frustrated teacher as the evening progressed, as though dismayed by his students' failure to grasp the fundamental lessons he had spent hours teaching.
Tottenham's manager did not appear startled when his worst fears were realised as the 19-year-old Josh Coburn scored a magnificent, highly earned winner deep in extra time, pushing Chris Wilder's excellent side into the sixth round.
Although Conte's Tottenham – and in particular Harry Kane – were far from their best, credit must be given to their carefully organised Championship opponents, particularly Jonny Howson.
Although Kane had a goal disallowed for offside in the second half, Boro, who beat Manchester United on penalties in the previous round, finished the stronger side, indicating that they would not be out of their depth in the Premier League.
"It was incredible, a fantastic result for our football club," said Wilder, who was overjoyed to play in front of the Riverside's first capacity crowd in five years, close to 35,000. "It's fantastic to have beaten a top team with a fantastic manager – and it's a fantastic occasion for Josh."
"We wasted a golden chance to get to the quarter-final," Conte stated. There is a sense of disappointment. We didn't take any risks. Middlesbrough earned the right to advance to the next round. We congratulate them. However, we should have ended the game sooner. There are far too many ups and downs in our lives. To make our team more stable, I need to be patient and work really hard. We need to get better. I have to find the best answer; the coach may need to use the stick at times."
Conte is rumoured to emulate Wilder's tactical three-at-the-back template, as both managers fielded wing-back-driven teams. However, Howson's assignment in a deep-lying midfield role proved crucial, and he played a significant role in guaranteeing Conte, who started the 4-0 triumph at Leeds last Saturday, would not be lifting the FA Cup this season.
The first half was not exactly overflowing with chances, with the exception of Dael Fry making a crucial interception to thwart Kane after Ryan Sessegnon moved with menace from left wing-back. Boro's disciplined side, which included some decent midfield cameos, including Matt Crooks, dominated possession but kept things close. Wilder's players kept their cool and didn't take any extra attacking risks, as Spurs were willing to play primarily on the counterattack.
Isaiah Jones frequently appeared the home player most capable of penetrating behind Conte's backline in the lack of much goalmouth activity – even though Matt Doherty circled Boro goalkeeper Joe Lumley only to shoot wide – as he eventually dominated his interesting subplot with Sessegnon.
Jones collapsed in close proximity to Sessegnon as Duncan Watmore surged past three visitor defenders. The Riverside demanded a penalty, but referee Darren England was unconvinced, dismissing Boro's desperate shouts but, maybe leniently, sparing Jones a yellow card.
That incident seemed to elicit some irritation among Spurs, and Lumley did well to divert Eric Dier's slightly curving free-kick for a corner immediately after. Dier and his teammate Ben Davies, in particular, were exceptional performers for Conte. After connecting with a flick-on from the next corner, Kane felt he had put his team ahead, but an offside flag denied him.
Overall, the unusually angry England centre-forward struggled to achieve the imperious heights he attained at Leeds, and his slipping while taking a perilously positioned freekick seemed to epitomize his very mediocre evening.
Howson came close to showing him how to accomplish it by curving a dead ball fractionally wider than his own.
Conte went through his entire repertoire of sorrowful technical area expressions as a result, and Tottenham's manager moved to a back four after the unmarked Arsenal loanee Folarin Balogun lent back and shot off target when well positioned.
With Wilder having done the same, Boro closed the first 90 minutes strongly, with Hugo Lloris saving from Jones, Crooks, and Marcus Tavernier, while Howson squandered a golden opportunity in extra time.
Coburn was finally able to break the stalemate. The teenager, who came to Boro after being released by Sunderland, was barely off the bench when he collected Crooks's smart cross and, holding off Cristian Romero, smashed a soaring, angled effort past Lloris and into the top corner.