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The hosts held the lead on two occasions, but a penalty from Sergio Aguero and a late Gabriel Jesus header earned the Blues a 2-2 draw in a frantic battle at The Riverside.
With Manchester United and Arsenal also failing to win over the weekend, hopefully will be a case of not too damage done in the battle for a top four finish..
City couldn’t have started much brighter with a scintillating move down the left that almost resulted in goal with just seconds on the clock.
A combination of Aleks Kolarov, Fernandinho and Gael Clichy worked the ball to Sergio Aguero who drove into the box and crossed for Gabriel Jesus but the Brazilian’s connection wasn’t strong enough and his attempt flashed wide.
The Blues continued to look for the opening goal and Aguero went close as he cut inside his marker and curled a rising drive just over the bar.
At that stage, City deserved to be ahead but a familiar tale of not converting early possession and chances into goals and gradually, Boro started to work their way into the game.
The first real chance for the hosts came on 13 minutes when Alvaro Negredo rasped a low shot across goal from close range when he should have perhaps tested Willy Caballero.
Boro continued to create half-chances but it was City who again went close on 36 minutes as Nicolas Otamendi’s excellent cross picked out Gabriel Jesus in the box but he was perhaps put off by the challenges around him as he headed harmlessly wide.
It was to prove a costly miss as Middlesbrough broke the deadlock in their next attack, just seconds later.
George Friend led a quick counter-attack but his cross didn’t look particularly dangerous as it drifted towards the edge of the City box, but Negredo beat a flat-footed defence to the ball and hit a powerful shot in off the post as he slipped to put Boro ahead.
With the Blues’ Champions League aspirations still in the balance, defeat at The Riverside was certainly not on the agenda.
With just four minutes of the second half played, Guardiola brought on wingers Raheem Sterling and Leroy Sane in a bid to inject more pace and creativity down the flanks.
It almost paid off immediately as Sterling skipped past two defenders before seeing his powerful shot blocked.
The Blues had upped the tempo and some of the Boro challenges became increasingly desperate as the half wore on with Sane and De Bruyne both hacked down by over-zealous Adam Forshaw challenges within the space of a few minutes that should have seen the Boro man heading for an early bath.
City’s dominance was finally rewarded in the 68th minute when De Roon’s challenge on Sane was deemed a penalty by referee Kevin Friend – much to the chagrin of the Boro players, several of whom picked up yellow cards as a result of their protestations.
Aguero made no mistake from the spot to put the Blues level, but despite a period of City pressure following the equaliser, it was the hosts regained the lead on 79 minutes.
Otamendi’s foul on Adama Traore resulted in a free-kick on the edge of the Blues’ box. Stewart Downing’s shot was palmed away by Caballero but the ball was only half-cleared and eventually found its way to Calum Chambers who poked home from close range.
It was a sucker punch that few expected and City were suddenly and unexpectedly back on the ropes.
Boro, driven by a passionate home crowd and the knowledge they were in the last chance saloon in many ways regarding relegation, threw caution to the wind in a bid to seal three points.
The Blues, however, dug deep and again fought back to level.
With 85 minutes on the clock, Aguero looking for options in the box, floated a terrific cross towards Gabriel Jesus who rose higher than anyone else to nod past Brad Guzan and make it 2-2.
City laid siege on the Boro goal in the time that remained but the relegation-threatened Teessiders managed to hang on for a point that does little for their hopes of survival.
Sane’s run into the box drew the challenge from De Roon and the referee’s decision to award a penalty undoubtedly changed the course of the game.
It also turned the final 20 minutes or so into a tinderbox, fiery affair with the home side convinced they’d been hard done to.
Little has changed in the battle for a top four spot with Manchester United drawing with Swansea. Arsenal losing to Spurs while Liverpool Watford on Monday.
City will host Crystal Palace next weekend with a 12.30pm start against the Eagles.
Palace are not mathematically safe and will look to repeat their excellent away performances against Chelsea and Liverpool when they visit Etihad Stadium.
The Blues, meanwhile, need nothing less than a win given today’s draw.
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