The German side took the lead through hotshot Hugo Ekitike after five minutes to threaten more misery for Ange Postecoglou and his men, but Spurs show great spirit to equalise through Pedro Porro and dominate the game. If it had not been for some wasteful finishing and an exceptional performance from Eintrach's stand-in goalkeeper Kaua Santos, the home side could have taken a healthy lead to Frankfurt next week.
Instead they will have to hope they can avoid sloppy mistakes, show the same spirit and find their finishing boots if they are to reach the semi-finals.
Shortly before kickoff, the big screens around the stadium showed an impressive montage of Tottenham's glory years in Europe, winning three trophies in 22 years, and the club's trumpeter led a rousing version of 'When the Spurs go marching in'. The stadium announcer asked supporters to make themselves heard for the club's biggest game of the season, and there was a sense of all or nothing for Ange Postecoglou and his men.
Barely five minutes in, the mood among Tottenham's fans was punctured as Etikite, Eintracht's outstanding forward, put them 1-0 ahead. James Maddison was caught in possession midway inside the Frankfurt half and Ellyes Skhiri set Ekitike away down the left wing. The French striker cut inside Porro, advanced towards the penalty area unchallenged and placed a low shot in the far corner of goal. It was stunningly simple and symptomatic of how defensively fragile Tottenham are.
Frankfurt's large and noisy band of fans, who hardly let up with their songs and drumbeats throughout the game, went into overdrive, while home supporters were stunned.
But Tottenham got themselves back into the game by being patient and persistent. Porro hit a long crossfield pass to Heung Min Son, who took the ball down perfectly but hit his ensuing cross into the arms of Santos.
Dominic Solanke had a glancing header saved, and later chipped in a cross that was headed over his own bar by Arthur Theate. Solanke's more significant contribution came in the 26th minute when he chased down a hopeful forward punt and laid the ball into Maddison's path. The England midfielder jinked to the byline and cut the ball back for Porro to divert it over the line with a cheeky backheel.
Spurs came out fired up for the second half and could have scored three times inside 15 minutes. Lucas Bergvall crashed a shot against the crossbar from 30 yards, Santos made a superb save to keep out Son's curling shot, and then Rodrigo Bentancur headed against the bar from the ensuing corner.
Bentancur had another header saved and Solanke spooned a shot high over the bar, before failing to find Johnson wih a low cross in front of goal. Both Postecoglou and Dino Toppmoller made a rash of substitutions in the closing stages to protect their positions, and there was still time for Santos to deny Tottenham once again, tipping Micky Van de Ven's header over the bar in stoppage time.
Spurs still have a chance of progressing, but they will need to make the most of their chances in Germany next week.
TOTTENHAM HOTSPUR: 4-3-3 Vicario7; Porro 6, Romero 6, van de Ven 7, Udogie 6 (Spence 79); Bergvall 8, Bentancur 7, Maddison 7 (Sarr 79); Johnson 6, Solanke 6 (Richarlison 87), Son 6 (Tel 79).
FRANKFURT: 4-2-3-1 Santos 8; Kristensen 6, Koch 6, Theate 6, Brown 6; Skhiri 6, Tuta 6; Gotze 4, Larsson 6, Bahoya 6 (Chaibi 70); Ekitike 7 (Wahi 89) Ref: Szymon Marciniak (Poland) 5/10