Tottenham Hotspur have registered a 1-0 win over Manchester City in the first leg of their Champions League quarter-final, but it was not a night of positives for Mauricio Pochettino side.
Son Heung-min has given Spurs a narrow advantage ahead of next week's reverse fixture at the Etihad Stadium, but Harry Kane suffered what appears to be another ankle ligament injury which could potentially end his season.
Both teams showed their qualities during a fast opening in North London, but it was Spurs who created the first opportunity of the contest as Dele Alli fired a volley marginally over the crossbar after meeting Moussa Sissoko's cross.
However, it was not long before City were awarded a controversial penalty. Raheem Sterling's shot was deflected wide of the post by Danny Rose, but the incident went to VAR before the referee deemed that Rose had handled the ball inside the area.
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Rose was also booked for his part in the incident, but the left-back and his side will feel that justice quickly followed as Hugo Lloris dived to his left to keep out Sergio Aguero's penalty.
Spurs and the home crowd had been left frustrated and relieved in equal measure, but Pochettino's players managed to channel their emotions in a positive way for the remainder of the first half.
Kane saw a shot punched clear by Ederson from 15 yards out, while the City backline were forced to make a number of timely blocks and interceptions to keep their hosts at bay.
Aguero had been relatively ineffective at the other end of the pitch, but the Argentine did send two efforts wide of the target during the closing stages of the first half.
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City went onto the front foot after the restart with Aguero managing to find Sterling on the opposite side of the penalty area, but the winger saw his low effort parried away by Lloris.
Spurs responded through two shots from Son, but a speculative effort from distance which went narrowly wide was followed by a tame strike that Ederson comfortably claimed to his right.
The home team were in the ascendancy, but that momentum was quickly halted as Kane was forced down the tunnel having come off worse in a challenge with Fabian Delph on the touchline.
Pochettino was furious with Delph's part in the tackle, but replays suggested that little blame could be placed on the City man despite Kane having twisted his ankle.
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A lull in the contest followed as both managers contemplated whether to stick or twist, and it was City who were making the greater effort to open the scoring by committing men forward.
However, Spurs rallied to take the lead with 12 minutes left. Son initially did well to beat the offside trap and keep the ball in play, but the South Korean was given too much space to get into a shooting position and fire low under Ederson from eight yards.
Pep Guardiola's side failed to apply much pressure during the closing stages of the game, but the Spaniard will be relatively content that his team face just a one-goal deficit after a largely laboured display in England's capital.
TOTTENHAM HOTSPUR (4-2-3-1): Lloris; Trippier, Alderweireld, Vertonghen, Rose; Winks (Wanyama 81'), Sissoko; Eriksen, Alli (Llorente 87'), Son; Kane (Lucas Moura 58')
MANCHESTER CITY (4-3-3): Ederson; Walker, Otamendi, Laporte, Delph; Fernandinho, Gundogan; D.Silva (De Bruyne 89'); Mahrez (Sane 89'), Aguero (Gabriel Jesus 71'), Sterling
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