Tottenham have work to do to reach the Europa League semi-finals after they were held to a 1-1 draw at home to Eintracht Frankfurt in the first leg of their last-eight tie.
Ange Postecoglou watched Spurs go behind after six minutes through Hugo Ekitike’s fine long-range strike, but Pedro Porro pulled them level midway through the first half with a sumptuous back-heel finish.
The Premier League outfit upped the ante after the break with Lucas Bergvall and Rodrigo Bentancur hitting the woodwork, while Frankfurt’s back-up goalkeeper Kaua Santos produced crucial saves to deny Son Heung-min, James Maddison and Micky van de Ven to leave the tie finely-poised ahead of next Thursday’s second leg in Germany.
This was Tottenham’s first European quarter-final since 2019, but a torrid domestic campaign meant it was another two-legged tie built up as make-or-break for Postecoglou, who stated on Wednesday the “general sentiment” was that even winning this competition may not save his job.
Spurs’ bid to make the last four got off to the worst possible start when Frankfurt delighted their bouncing travelling fans with a sixth-minute goal.
After Maddison lost possession to Ellyes Skhiri, the visitors produced a slick counter-attack and Ekitike cut inside Porro before arrowing a 22-yard effort into the bottom corner for his 20th goal of the season.
The hosts had to survive two corners in quick succession shortly afterwards, but did begin to regroup with two dangerous crosses by Son and Dominic Solanke enough to get the home supporters briefly off their feet.
A goal was required to light the touchpaper for Tottenham and an unlikely source provided it in the 26th minute.
Son and Solanke initially combined before the latter found Maddison, who burst past Skhiri and cut back for Porro to brilliantly back-heel the leveller for only his third goal this term.
It sparked big celebrations from Spurs’ single-tier South Stand but another chance went begging when Son blazed over a quick free-kick.
Ekitike bookended the half with a weak effort straight at Guglielmo Vicario before a crucial Bergvall intervention denied him another chance immediately after the break.
Bergvall was the catalyst for a momentum shift as he superbly turned away from two opponents and sent a 55th-minute piledriver against the crossbar to spark a period of Spurs dominance.
It was followed by a flying save from Kaua to thwart Son’s curled effort before a Bentancur header from the resulting Porro corner went over via the crossbar.
A low effort by Maddison, which Kaua did well to block, concluded a spell of four chances in as many minutes that ultimately did not result in a second Tottenham goal.
Jean-Matteo Bahoya hooked over for Frankfurt not long after in a reminder of their threat before another Bentancur header was saved by Kaua.
Postecoglou rolled the dice late on with Son and Maddison withdrawn and a stoppage-time winner almost followed but Van de Ven’s close-range header from a Bentancur knock-down was impressively tipped over by Kaua.