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In a game played out amidst awful conditions of driving wind and freezing rain, City assumed early control through Taylor Richards' strike.
But a red card for City forward Ian Poveda just after the half hour turned the game on its head.
And two goals from Spurs striker Kazaiah Sterling late on in either half saw the visitors make their numerical advantage pay, ending City’s run of three straight victories.
The match got under way in dreadful conditions amidst freezing temperatures with City playing against an Arctic wind.
There was an early reshuffle for City with central defender Eliaquim Mangala forced off with a leg knock with barely eight minutes gone.
Spurs almost drew first blood with Kazaiah Sterling’s shot just skimming the far post but, after that, the Blues soon took a firm grip on the game.
And on 13 minutes our supremacy was rewarded. Rabbi Matondo beat the Spurs back line and his cross ricocheted out to Taylor Richards who, from 12 yards, made no mistake.
City kept up the momentum with a Richards free-kick being blocked before the midfielder then shot over from 25 yards.
However, the balance of the game then swung in the visitors favour after a flashpoint incident saw City Ian Poveda shown a straight red card by referee Martin Wood.
The striker tangled with George Marsh and, after a coming together, the Spurs man dramatically fell to the floor in front of Wood who showed a straight red to Poveda.
Spurs made their numerical advantage tell just before the break when Sterling latched on to a vicious rebound before coolly slotting a low shot past Grimshaw.
The visitors maintained the upper hand after the break with Sterling in particular proving a real handful.
Twice the centre forward evaded the City defence only to direct close-range headers wide.
For the Blues, Rabbi Matondo proved our main attacking outlet thanks to his pace and trickery.
City were also indebted to keeper Daniel Grimshaw who produced two fine saves to deny Dylan Duncan and Sterling.
But just when it looked as if the game would end all square, Spurs struck with nine minutes left.
George Marsh fired in a dangerous cross and danger man Sterling evaded the Blues defence to bundle the ball home past Grimshaw and so seal the victory.
Daniel Grimshaw was in goal shielded by a back four of Alpha Diounkou, Colin Rosler, Eliquim Mangala and Nathanael Ogbeta.
The midfield saw Iker Pozo operate as the shield with Taylor Richards and Felix Nmecha further forward.
Rabbi Matondo and Luke Bolton provided the width with Ian Poveda deployed upfront.
The defeat sees City drop down a place to fifth in the table on 20 points.
The young Blues break off for Christmas now and are next in action at home to West Ham on Monday, January 7 in Premier League 2.
Checkatrade Trophy Round 3 draw details