It took Manchester City over 100 shots and more than nine hours but Pep Guardiola's men finally scored a goal at the Tottenham Hotspur Stadium.
Nathan Ake got it 88 minutes into Friday's FA Cup clash to send City through to the fifth round for the ninth season in a row.
City's 1-0 win was their sixth game at Tottenham's new stadium. Spurs had won each of the first five to nil.
Son Heung-min had scored in four of those five Spurs wins over City but the South Korean star was unavailable on Friday as he is currently at the AFC Asian Games.
City thought they had broken their duck when Oscar Bobb tapped home from ultra close range in the fifth minute after Phil Foden's initial shot had been saved by Guglielmo Vicario.
However, a lengthy VAR review eventually ruled that Bobb had been marginally offside when Foden struck the ball.
Spurs were later hoping that the VAR would save them again by disallowing Ake's scrambled winner.
Ake bundled the ball over the line after Vicario had flapped at a Kevin De Bruyne cross.
Replays were studied to see if Vicario had been fouled by Ruben Dias but the video judges ruled in City's favor.
De Bruyne had entered the game as a substitute 20 minutes into the second half.
Tottenham's creator-in-chief then came moments later but failed to get into the contest after 81 days out with an ankle injury.
De Bruyne should have scored himself before Ake's opener but the Belgian fired wide following an error by Pierre-Emile Hojbjerg.
City's win at Spurs was one of four FA Cup games on Friday.
Elsewhere, Aston Villa drew 0-0 at Chelsea. Bristol City's match with Nottingham Forest also ended goalless, while Sheffield Wednesday and Coventry finished 1-1..
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