Tottenham 1-1 Eintracht Frankfurt | Highlights
Hugo Ekitike opened the scoring for the visitors, but Pedro Porro's equaliser means it's all square heading into the second leg.
Ange Postecoglou's bid to end Tottenham's long trophy drought is delicately poised after a 1-1 draw against Eintracht Frankfurt in the Europa League quarter-final first leg on Thursday.
Postecoglou's troubled side trailed to Hugo Ekitike's early goal in north London, but Pedro Porro hauled them level before half-time.
Tottenham laid seige to the Frankfurt goal in the second half but couldn't find a winner after hitting the woodwork twice.
The result means under-fire Tottenham boss Postecoglou must mastermind a memorable victory in the second leg in Germany on April 17 to keep alive his hopes of winning the club's first trophy since the 2008 League Cup.
"It was disappointing to concede the way we did. The biggest blow we had was conceding so early. That kind of played into their hands," Postecoglou said.
"But even before that, I thought we were well in control of the game. I thought it would bring fruit in the second half and it did in every aspect but goals. I can't ask any more of the lads."
The winner of the tie will face Bodo/Glimt or Lazio in the semi-finals in May, with the Norwegian club taking a 2-0 lead into the second leg against the Italians.
"On any other night we go away with a comfortable victory. We have to go there. If we repeat that performance we give ourselves a chance," Postecoglou said.
"I don't expect the second game to be to open, it'll be cagey affair and it'll come down to moments."
Postecoglou brashly claimed earlier this season that he always wins a trophy in his second campaign, a statement that has made him a hostage to fortune throughout Tottenham's turbulent run.
The Australian has endured such intense criticism lately that he joked on Wednesday that he would still be "gone" at the end of the season even if he did win the Europa League because his approval rating is so low with Tottenham supporters.
Against a backdrop of constant fan protests against chairman Daniel Levy, Tottenham are languishing in 14th place in the Premier League, leaving them in danger of their worst finish since 1993-94, when they came 15th.
Frankfurt sit third in the Bundesliga table and are hoping to return to the Europa League final after winning the tournament in 2022.
- Postecoglou relief -
Befitting their respective league positions, Frankfurt started with more confidence and purpose.
Ekitike had scored 19 goals and provided eight assists in 40 appearances prior to Thursday's game, making him Frankfurt's danger-man and a transfer target for several English clubs.
But Tottenham failed to heed the warning as the 22-year-old struck in stunning style after just six minutes.
James Maddison conceded possession and Frankfurt launched a blistering break that climaxed with Ekitike accelerating past Porro to curl a fine finish into the bottom corner from the edge of the area.
Tottenham's stirring response was a welcome boost for Postecoglou as Son Heung-min's pin-point cross reached Dominic Solanke for a header that was clutched by Frankfurt keeper Kaua Santos.
If Ekitike's opener was an eye-catching moment, Porro's 26th minute leveller was even more artistic.
Maddison danced through the Frankfurt defence and cut his pass back to Porro, who produced a sublime back-heeled flick that flashed past Santos from six yards.
Postecoglou had his head in his hands when Tottenham's young midfielder Lucas Bergvall lashed a fierce drive against the crossbar from 25 yards.
That was the start of a sustained spell of second-half pressure from Tottenham.
Santos made a superb save to claw Son's curler over before Rodrigo Bentancur's header from the resulting set-piece cannoned off the bar.
Maddison's close-range strike forced Santos to make another good save before Micky van de Ven's header was brilliantly palmed over by the Frankfurt keeper as the first leg ended on a knife edge.