Tottenham's Europa League hopes hang by a thread after a controversial defeat by 10-man PAOK Salonika.
The Greek side raced into a 2-0 lead through a Dimitris Salpingidis header and a Stefanos Athanasiadis tap in.
Luka Modric's first-half penalty gave Spurs hope after Kostas Stafylidis was sent off for handling on the line.
Jermain Defoe had a goal ruled out, leaving Spurs needing to beat Shamrock Rovers and rely on Rubin Kazan dropping points in the final group game.
Spurs, who travel to Dublin on 15 December, also need a six-goal swing in goal difference if they are to sneak into the knockout phase, while PAOK - who host Rubin in their final match - have sealed qualification.
But manager Harry Redknapp will bemoan the contentious decision to disallow Defoe's late effort, with confusion reigning over whether it was chalked off for offside or Defoe's late tackle on Pablo Contreras 10 seconds earlier.
With the injured Contreras floored on the line, Spurs played on and scored, only for it to be ruled out after a period of chaotic indecision between the officials.
Redknapp only partially maintained his policy of blooding his youngsters in the Europa League as he sprinkled Modric, Defoe and Aaron Lennon to a team that also included Harry Kane, 18, and Danny Rose, 21.
But Spurs, whose sparkling form has seen them rise to third in the Premier League, looked fragile and languid against PAOK, who carved them open with their first meaningful attack.
DID YOU KNOW?
PAOK met Tottenham's north London rivals Arsenal in the 1997 UEFA Cup first round, winning 1-0 in Salonika then drawing 1-1 in London. That was their only previous tie against an English side
William Gallas, making just his second start of the season, overran the ball in his own half and allowed Giorgos Georgiadis to exploit the vacant space down Tottenham's right.
Goergiadis coaxed an inch-perfect cross to Salpingidis, who wrong-footed home goalkeeper Heurelho Gomes with his header.
Spurs controlled possession but looked exposed every time they lost the ball - and were punished again eight minutes later.
Vedran Corluka allowed the lively Georgiadis too much space on the left again, and his low cross was steered in at the far post by Athanasiadis to give PAOK's raucous travelling support even more reason to be heard.
The sight of substitutes Kyle Walker and Gareth Bale warming up on the touchline seemed to give Spurs the jump start they needed, and Defoe and Kane each drew saves out of goalkeeper Kostas Chalkias.
With half time approaching, Spurs were handed the lifeline they needed when Kostas Stafylidis was dismissed when Kane's shot struck the defender's arm on the goalline and Modric calmly stroked in the resulting penalty.
PAOK possessed genuine attacking threats in Georgiadis and Giorgos Fotakis, but their influence diminished as Spurs ramped up the pressure in the second half.
Kane headed over from Rose's cross and Steven Pienaar slammed his shot into the advertising hoardings as Tottenham looked to make their dominance count.
Walker and Bale were introduced to add to some urgency to Tottenham's wing play, but PAOK defended heroically at times, throwing themselves in the way of the ball as Spurs maintained an extraordinary spell of pressure.
The game's defining moment came when Dutch referee Bas Nijhuis ruled out Defoe's effort, leaving Spurs needing an unlikely combination of results to progress.
- 01 Gomes
- 13 Gallas
- 19 Bassong
- 22 Corluka
- 07 Lennon
- 14 Modric
- 25 Rose (Bale - 62' )
- 29 Livermore
- 40 Pienaar (Walker - 67' )
- 18 Defoe
- 37 Kane (Falque - 71' )
- 23 Cudicini
- 03 Bale
- 28 Walker
- 31 Townsend
- 43 Fredericks
- 46 Carroll
- 27 Falque
- 01 Chalkias
- 13 Malezas
- 15 Contreras (Cirillo - 81' )
- 03 Stafylidis Dismissed
- 05 Pablo Garcia
- 18 Fotakis
- 25 Lazar (Arias - 83' )
- 77 Etto
- 07 Georgiadis (Sznaucner - 62' )
- 09 Salpingidis
- 33 Athanasiadis Booked
- 91 Kresic
- 08 Cirillo
- 27 Sznaucner
- 04 Balafas
- 21 Ivic
- 85 Arias
- 14 Papazoglou