Manchester City 1 Middlesbrough 1

A fortnight after Aitor Karanka’s side held Arsenal to a draw on their own turf, they were at it again as they frustrated Pep Guardiola’s leaders at the Etihad.

A spirited rear-guard action looked to have been undone when Sergio Aguero fired City into a first-half lead, but after the Argentinian wasted a great chance to make the game safe with five minutes left, Boro struck in the second minute of stoppage time.

De Roon headed home George Friend’s cross to claim his first goal in English football and frustrate a City side who had brushed aside Barcelona just four days earlier.

Having watched his side hold Arsenal to a goalless draw last month, Karanka understandably stuck with the same blueprint as Boro faced the league leaders.

De Roon replaced the suspended Gaston Ramirez in an attempt to bolster the midfield, with Karanka reverting to a 4-5-1 formation that saw the Teessiders regularly pull nine outfield players back into their own box.

The ploy was an attempt to frustrate City, and it was effective to a degree. Unlike at the Emirates, however, Boro failed to make it to half-time without conceding.

That their defence was unbreached in the opening 43 minutes was largely due to the excellence of Victor Valdes, with the former Manchester United goalkeeper making two superb saves as City gradually ratcheted up the pressure.

Valdes’ first involvement was routine as he claimed a long-range effort from Aleksandar Kolarov midway through the first half, but he was extended much more strenuously shortly after the half-hour mark as he flung himself to the ground to keep out Aguero’s effort after the Man City striker had jinked past two defenders in the box.

Four minutes later, and Valdes was at it again, producing a brilliant point-blank save to keep out David Silva’s effort after the Spaniard had met Jesus Navas’ deflected shot.

Had Boro been able to make it to the interval on level terms, they might well have fancied their chances of repeating their result from the Emirates last month.

As it was, however, their defence was breached two minutes before the break. Kevin de Bruyne delivered an excellent slide-rule cross from the right, and Aguero stole between Boro’s two centre-halves to prod home.

City almost claimed a second goal with the final kick of the first half, but Navas’ shot from the edge of the area clipped the outside of the right-hand post.

Boro failed to record a shot of any description in the opening 45 minutes, but they emerged from the interval with a much more positive attitude and tested Manchester City goalkeeper Claudio Bravo on two separate occasions within five minutes of the restart.

The first effort was an audacious one, with Alvaro Negredo spotting Bravo off his line and attempting to beat him from the halfway line. The ball was going in, but a back-pedalling Bravo successfully tipped it over the bar.

The Chilean goalkeeper was called into action again five minutes later, with Boro finally enjoying some extended time in the City half. Adama Traore played in Adam Forshaw on the overlap, and the midfielder’s shot was creeping in at the near post before Bravo got down to deal with it.

With Forshaw playing much further forward, Boro were a more threatening attacking proposition in the second half, but City continued to dominate possession and Ilkay Gundogan fired narrowly wide from the edge of the area shortly after the hour mark.

Aguero headed over as he met de Bruyne’s cross, but Boro might have grabbed an equaliser with 16 minutes left had Stewart Downing displayed marginally more composure.

Clayton played the former England international into the area, but Downing could only drag a shot across the face of goal and beyond the far post.

Forshaw was denied by a brilliant tackle from John Stones shortly after, with the England defender stealing the ball away from his opponent as he shaped to connect with Negredo’s shot, and Boro’s first change saw Viktor Fischer replace Downing on the left-hand side.

Aguero side-footed over when he was completely unmarked in the box with five minutes left, and the miss proved costly as Boro struck in the second minute of stoppage time.

George Friend swung over an inviting cross from the left, and having powered into the box, de Roon planted a back-post header past Bravo.

It was a brilliant header from the Dutchman, provoking wild scenes in the sold-out away end and the Boro dug-out, and secured the Teessiders a hugely creditable point.

Man City (4-2-3-1): Bravo; Zabaleta, Stones, Kolarov, Clichy; Fernandinho, Gundogan (Nolito 74); Navas (Garcia 86), de Bruyne, Silva; Aguero (Iheanacho 90).

Subs (not used): Caballero (gk), Kompany, Maffeo, Sane.

Middlesbrough (4-5-1): Valdes; Barragan, Chambers, Gibson, Friend; Traore (Stuani 90), Clayton, de Roon, Forshaw, Downing (Fischer 78); Negredo.

Subs (not used): Guzan (gk), Espinosa, Fabio, Leadbitter, Nugent.