Tottenham had to settle for a point at Frankfurt after enduring a frustrating goalless draw from their Champions League Group D fixture.
Spurs were eager to bounce back following Saturday’s humbling loss to rivals Arsenal and produced a much-improved display but failed to show enough quality in the final third.
Elsewhere in Group D, Olympique de Marseille secured their first Champions League win of the season when they recovered from a shaky start to outclass 10-man Sporting Lisbon 4-1 in an incident-packed Group D encounter at an empty Stade Velodrome on Tuesday.
In Group A, Giacomo Raspadori netted twice as Napoli came from behind to deliver a masterclass and score a runaway 6-1 win at 10-man Ajax Amsterdam. Captain Giovanni di Lorenzo, Piotr Zielinski, Khvicha Kvaratskhelia and substitute Giovanni Simeone added the other goals for the Italian league leaders, after Mohammed Kudus had given the hosts the lead inside the opening 10 minutes. Liverpool put their recent stutters behind them to comfortably beat Rangers 2-0 in the Champions League on Tuesday and move into second spot.
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In Group B, goals from Club Brugge forwards Kamal Sowah and Ferran Jutgla saw the Belgians beat Atletico Madrid 2-0 at home on Tuesday to extend their unbeaten run in Champions League Group B this season. Porto beat Bayer Leverkusen 2-0 for their first win of the campaign with goals from Zaidu Sanusi and Wenderson Galeno.
In Group C, Bayern Munich struck three times in the opening 21 minutes en route to a 5-0 demolition of Viktoria Plzen in the Champions League on Tuesday to stay top of Group C and set a record for the longest unbeaten run in group matches. Inter Milan bounced back after two consecutive losses in Serie A with a crucial Champions League 1-0 win against Barcelona on Tuesday thanks to a Hakan Calhanoglu goal.