Cape Town - Monaco booked their place in the UEFA Champions League last 16 as they beat an out-of-sorts Tottenham 2-1 at Stade Louis II on Tuesday.
The first half was a scrappy affair with Spurs bossing possession but failing to create any clear-cut chances, as the hosts looked more threatening on the counter.
The visitors were presented with a glorious opportunity to break the deadlock after just six minutes, though, when Dele Alli sent Son Heung-Min through on goal, but the South Korean forward tried to go around Danijel Subasic, who got a touch on the ball to force him away from goal.
Tiemoue Bakayoko had the Principality outfit's first chance two minutes later, but his tame shot was easy for Hugo Lloris, who then denied Radamel Falcao from 12 yards out moments later after Eric Dier had brought down Fabinho inside the area to concede a penalty.
The hosts continued to ask questions of the Spurs defence as Thomas Lemar hit a firm shot straight at Lloris from distance, while Falcao fired wide from just outside the area before Sidibe curled an effort narrowly wide of the far post from the right-hand side of the box.
Valare Germain then went close as he latched onto a long ball over the top before flashing his shot inches past the left post from an acute angle on the right.
The final chance of the first half saw Jemerson head wide at the back post from a corner in the 41st minute, with the north Londoners failing to get a single attempt on target.
The second half started with a bang as Sidibe opened the scoring with a close-range header from Benjamin Mendy's dangerous cross on 48 minutes, but Spurs were level within three minutes as they won a penalty for Kamil Glik's foul on Alli.
Kane's spot-kick had enough power on it to beat Subasic, who got a glove to the ball. However, Monaco hit back instantly as Lemar drilled his shot past Lloris after controlling a cross from the right - restoring their lead just 16 seconds from the kick-off.
Lloris was called into action again on 63 minutes to deny Bernardo Silva, who had cut back inside from the right before getting off a shot, and the French keeper pulled off a brilliant reaction save five minutes later to tip over Glik's first-time effort from six yards out as he connected with a free-kick.
Christian Eriksen had a rare chance for the visitors on 71 minutes when he cut inside from the left and saw his shot deflected behind for a corner, but Lloris was soon tested again as he parried away a firm strike from Falcao, who was played in by a ball over the top.
Kane tested Subasic with a snapshot from the left-hand side of the box in the closing stages and Alli spurned a golden chance to equalise moments later from a corner as he stabbed wide at the back post from close range under pressure from Mendy.