As the evening wore on Antonio Conte resembled an increasingly disappointed teacher, apparently saddened by his class’s failure to absorb the basic lessons he had devoted hours to imparting.
Tottenham’s manager did not looked entirely surprised when his worst fears were realised and, deep in extra time, the 19‑year‑old Josh Coburn, after only 11 minutes on the pitch, scored a fine, richly deserved winner, propelling Chris Wilder’s impressive side into the sixth round.
Although Conte’s Tottenham – and Harry Kane in particular – were far from their best, considerable credit must go to their meticulously organised opponents from the Championship and, in particular, Jonny Howson, who shone in a defensive midfield role.
Although Kane had a second‑half goal disallowed for offside Boro, who won on penalties at Manchester United in the last round, finished the stronger side – suggesting they would not be out of their depth in the Premier League.
“It was amazing, a great result for our football club,” said Wilder, who was delighted to play in front of the Riverside’s first capacity, near-35,000 crowd for five years. “It’s brilliant to have beaten a top side with an outstanding manager – and a great moment for Josh.”
Conte said: “We lost a good chance to go to the quarter-final. There’s disappointment. We didn’t take our chances. Middlesbrough deserved to go to the next round. We compliment them. But we should have killed the game. We have too many up and downs. I have to be patient and work very hard to make this team more stable. We have to improve. I have to find the best solution; sometimes the coach has to use the stick.”
Wilder jokes that Conte likes to copy his tactical three-at-the-back blueprint and, sure enough, both managers fielded wing-back-propelled sides. Howson’s deployment in a deep-lying midfield role proved pivotal though and he played a key role in ensuring Conte, who fielded the side which started the 4-0 win at Leeds last Saturday, would not be lifting the FA Cup this season after all.
Except for Dael Fry making a vital interception to deny Kane after Ryan Sessegnon advanced with menace from left wing-back, the first half was not exactly replete with chances. Generally a disciplined Boro side featuring some decent midfield cameos, including Matt Crooks, hogged plenty of possession but kept things fairly tight. Retaining their composure, Wilder’s players took no unnecessary attacking risks as Spurs seemed content to play very much on the counterattack.
In the absence of much goalmouth action – even though Matt Doherty rounded the Boro goalkeeper Joe Lumley only to shoot wide – Isaiah Jones consistently looked the home player most capable of getting behind Conte’s backline as he ultimately dominated his intriguing subplot with Sessegnon.
When Duncan Watmore accelerated beyond three visiting defenders Jones promptly collapsed in close proximity to Sessegnon. The Riverside demanded a penalty but Darren England, the referee, was not fooled, swiftly dismissing Boro’s forlorn appeals but, perhaps leniently, allowing Jones to escape a yellow card.
That incident seemed to, briefly, bring out a certain indignation in Spurs and, shortly afterwards, Lumley did well to divert Eric Dier’s subtly curving free-kick for a corner. Significantly Dier and his fellow defender Ben Davies proved rare strong performers for Conte. Kane thought he had volleyed his side ahead after connecting with a flick-on from the ensuing corner but was denied by an offside flag.
Overall the unusually irritable looking England centre-forward struggled to hit the imperious heights he reached at Leeds and it seemed thoroughly emblematic of his rather indifferent evening when he slipped while taking a dangerously placed free‑kick.
Howson very nearly showed him how to do it, curling a dead ball of his own fractionally wide.
It left Conte running through his full repertoire of sorrowful technical area expressions and, immediately after the unmarked Arsenal loanee Folarin Balogun lent back and shot off target when well placed, Tottenham’s manager switched to a back four.
With Wilder having done likewise Boro finished the opening 90 minutes very much in the ascendant with Hugo Lloris saving from Jones, twice, Crooks and Marcus Tavernier , while Howson missed a sitter in extra time.
Eventually Coburn deservedly broke the impasse. The teenager, from just down the road in Bedale, and who joined Boro after being discarded by Sunderland , was not long off the bench when he met Crooks’s clever pass and, holding off Cristian Romero, lashed a rising, angled shot unerringly past Lloris and on into the top corner.
