Demba Ba’s late penalty for Besiktas denied Tottenham their first win in Group C of the Europa League.
The ex-Chelsea man converted after Vlad Chiriches handled in the area having let the ball slip through his legs.
Harry Kane gave Spurs the lead in the 27th minute when he surged forward before firing a low shot past keeper Tolga Zengin from the edge of the area.
Spurs keeper Hugo Lloris twice denied Olcay Sahan with brilliant saves, before tipping over an effort from Ba.
Both Besiktas frontmen were a constant menace for Tottenham, who were lucky not to lose to Slaven Bilic’s Turkish side.
The former Croatia manager would have been frustrated by the failure to secure a first group win and by the exceptional keeping of stand-in skipper Lloris.
The France international saved Spurs on three memorable occasions. He used his foot to divert Sahan’s goalbound effort wide and then sprung off the turf to tip over the striker’s loaded drive. His skills were then tested when he pushed Ba’s fierce close-range half-volley over the bar.
Lloris was finally beaten with a minute of normal time remaining, no thanks to team-mate Chiriches. A ball played for Sahan went under the Romania international’s legs before he handled.
The Senegal international stepped up to take the spot-kick, stuttered on his run before planting his effort past the Tottenham number one. It was his fifth goal in six appearances against the north London side.
Besiktas, second in the Turkish league, were more potent in attack than their counterparts. They managed 24 efforts on goal as opposed to six for Tottenham, who only had three on target.
One of those came from the boot of Kane. The under-21 international once again highlighted his potential with a superbly taken goal in the first half.
Having picked up the ball from Nabil Bentaleb, the forward turned his marker then drove forward before guiding a low shot into Zengin’s bottom-left corner.
Kane, who looked far more threatening than struggling frontman Roberto Soldado, also had a low angled drive saved by the Beskitas keeper at his near post.
The result means Tottenham have only two points from their first two group matches. Their next opponents are Group C leaders Asteras Tripoli.
Read more on BBC Sport