Tottenham missed the chance to move top of Group D in the Champions League after being held to a goalless draw by Eintracht Frankfurt.
It proved to be a wasteful day for Antonio Conte’s side, who registered just two shots on target from 11 attempts in Germany.
Harry Kane and Heung-min Son went closest for Spurs, but they have now failed to find the net in successive Champions League group games for the first time since the 2016-17 season.
Both sides remain on four points after three matches, and two behind Group D leaders Sporting CP following the Portuguese giants’ 4-1 thrashing by Marseille.
Emerson Royal fired a volley over after six minutes, while Kane was whiskers away from applying the finishing touch to a wonderful move as he narrowly avoided connecting with Son’s inviting cross.
Kane whipped a fierce 20-yard strike narrowly wide in the 28th minute. The England captain then turned provider with a neat flick that released Son, whose curling shot was also off target, before Ivan Perisic’s deflected effort spun inches wide.
Eintracht almost took the lead in spectacular fashion five minutes after the restart; Ansgar Knauff springing the offside trap before his acrobatic effort was blocked by Hugo Lloris.
Evan Ndicka produced a magnificent last-ditch intervention to deny Kane at the other end, while Son whipped an 18-yard strike wide.
Jesper Lindstrom fired a glorious opportunity to snatch the win over after Spurs were caught in possession on the edge of their penalty area, as the spoils were shared at Deutsche Bank Park.
What does it mean? Spurs end losing streaks despite stalemate
Tottenham are now without a win in six away European fixtures, but they did end a run of three straight defeats following the 0-0 draw.
Spurs also halted a four-game losing streak against German opposition, while Eintracht missed out on a fourth successive victory over an English side.
However, Conte’s side are without a win in the Champions League this season and require considerable improvement in the remaining three games, with the situation in Group D delicately poised.
Half a century for Son
Son became only the second Asian player to reach 50 Champions League appearances after compatriot Park Ji-Sung (54).
But despite registering three shots on goal – a tally only bettered by Kane – the former Bayer Leverkusen forward was unable to mark the occasion by finding the net on his return to Germany.
Kane streak ends
Kane arrived in this contest having scored in each of his four Champions League appearances against German opposition (five goals).
Although he recorded a game-high four shots, only Clement Lenglet (17) lost possession on more occasions for Spurs than the England skipper (16), who could not quite make the difference in front of goal.
The two sides renew their rivalry in the return fixture at the Tottenham Hotspur Stadium next Wednesday. Before then, both teams are on their travels this Saturday. Tottenham head to Brighton in the Premier League, while Eintracht are away at Bochum in the Bundesliga.