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
Live Text Commentary
Full Time The referee ends the match.90:00 +2:39
Direct effort from the free kick comes in from Gareth Bale, save made by Kostas Chalkias.90:00 +2:39 Booking
Booking The referee shows Stefanos Athanasiadis a yellow card for dissent.90:00 +2:33
Free kick awarded for an unfair challenge on Gareth Bale by Giorgos Fotakis.90:00 +1:39
Outswinging corner taken left-footed by Luka Modric from the left by-line, Effort from deep inside the area by Jermain Defoe misses to the right of the target.90:00 +1:20
Jermain Defoe takes a shot. Save by Kostas Chalkias.86:53
Jake Livermore challenges Bruno Cirillo unfairly and gives away a free kick. Direct free kick taken by Bruno Cirillo.84:01
Luka Modric decides to take the corner short, Effort on goal by Gareth Bale from just inside the penalty box goes harmlessly over the target.82:50 Substitution
Substitution Costin Lazar leaves the field to be replaced by Diego Arias.82:31
Iago Falque has an effort at goal from just outside the area which goes wide of the left-hand post.81:48
Outswinging corner taken by Luka Modric, Perez Pablo Garcia makes a clearance.80:31
Luka Modric takes the inswinging corner, Sebastien Bassong takes a shot. Blocked by Perez Pablo Garcia.80:10 Substitution
Substitution Bruno Cirillo replaces Pablo Contreras.76:04
Iago Falque takes a shot. Pablo Contreras manages to make a clearance. Jermain Defoe concedes a free kick for a foul on Pablo Contreras. Kostas Chalkias restarts play with the free kick.74:48
William Gallas gives away a free kick for an unfair challenge on Costin Lazar. Perez Pablo Garcia crosses the ball from the free kick left-footed from left wing.71:43
Gareth Bale fouled by Giorgos Fotakis, the ref awards a free kick. Luka Modric takes the direct free kick.70:38
Direct free kick taken by Perez Pablo Garcia.70:38 Substitution
Substitution Harry Kane goes off and Iago Falque comes on.70:38
Dimitris Salpingidis fouled by Harry Kane, the ref awards a free kick.69:44
Shot on goal by Gareth Bale from just inside the area clears the crossbar.
Substitution Kyle Walker is brought on as a substitute for Steven Pienaar.66:04
Jake Livermore has a shot on goal from outside the area which misses right.65:33
Inswinging corner taken right-footed by Luka Modric played to the near post, clearance by Pablo Contreras.65:05
Sebastien Bassong takes a shot. Stilianos Malezas gets a block in.64:07
Harry Kane crosses the ball, clearance by Pablo Contreras.62:32
Vedran Corluka gives away a free kick for an unfair challenge on Dimitris Salpingidis. Direct free kick taken by Perez Pablo Garcia.61:53 Substitution
Substitution Gareth Bale is brought on as a substitute for Danny Rose.61:26 Substitution
Substitution Georgios Georgiadis leaves the field to be replaced by Miroslaw Sznaucner.60:01
Corner taken right-footed by Luka Modric, Costin Lazar makes a clearance.59:16
Short corner taken by Luka Modric from the right by-line.58:49
Harry Kane takes a shot. Pablo Contreras gets a block in.56:28
Shot from just outside the penalty box by Steven Pienaar misses to the left of the target.54:40
The referee blows for offside against Jermain Defoe. Kostas Chalkias takes the free kick.53:10
Free kick awarded for an unfair challenge on Jake Livermore by Perez Pablo Garcia. Direct free kick taken by Vedran Corluka.52:18
Free kick awarded for a foul by Harry Kane on Pablo Contreras. Direct free kick taken by Pablo Contreras.51:45
The referee gives a free kick against Harry Kane for handball. Free kick taken by Kostas Chalkias.50:17
Close range headed effort by Harry Kane misses to the right of the goal.47:35
Outswinging corner taken by Luka Modric, Stefanos Athanasiadis fouled by William Gallas, the ref awards a free kick. Direct free kick taken by Kostas Chalkias.45:33
Free kick awarded for a foul by Oeliton Etto on Steven Pienaar.45:32
Luka Modric crosses the ball from the free kick right-footed from left wing. Harry Kane is flagged offside by the assistant referee. Kostas Chalkias restarts play with the free kick.45:32 Booking
Booking Booking for Oeliton Etto for unsporting behaviour.45:01
The referee blows his whistle to start the second half.45:00 +0:58 Half time
Half Time The players leave the pitch at half time.45:00
Handball by Jermain Defoe. Costin Lazar takes the direct free kick.40:53
Free kick awarded for an unfair challenge on Luka Modric by Oeliton Etto. Direct free kick taken by Luka Modric.40:16
Shot from just outside the area by Danny Rose misses to the left of the target.38:42 Goal scored
Goal! - Luka Modric - Tottenham 1 - 2 PAOK Luka Modric scores a placed penalty. Tottenham 1-2 PAOK Salonika.38:19 Dismissal
Dismissal Red card for Konstantinos Stafylidis.36:17
Jermain Defoe takes a shot. Save by Kostas Chalkias. Corner taken right-footed by Luka Modric, Vedran Corluka takes a shot. Clearance made by Konstantinos Stafylidis. Harry Kane takes a shot. Konstantinos Stafylidis gets a block in. Handball decision goes against Konstantinos Stafylidis.34:30
The referee blows for offside. Danny Rose takes the indirect free kick.33:06
A cross is delivered by Harry Kane, clearance by Konstantinos Stafylidis.31:39
Harry Kane produces a left-footed shot from deep inside the penalty box which goes wide of the left-hand post.30:40
Perez Pablo Garcia gives away a free kick for an unfair challenge on Harry Kane. Harry Kane takes the direct free kick.29:35
The referee blows for offside against Steven Pienaar. Kostas Chalkias takes the free kick.28:12
The assistant referee signals for offside against Stefanos Athanasiadis. Heurelho Gomes takes the indirect free kick.25:33
Stefanos Athanasiadis takes a shot. Blocked by Sebastien Bassong.23:16
Free kick awarded for an unfair challenge on Perez Pablo Garcia by Steven Pienaar. Direct free kick taken by Perez Pablo Garcia.22:22
Unfair challenge on Steven Pienaar by Costin Lazar results in a free kick. Luka Modric takes the free kick.21:48
Free kick awarded for an unfair challenge on Dimitris Salpingidis by Jake Livermore. Direct free kick taken by Oeliton Etto.18:13
Jermain Defoe produces a left-footed shot from just outside the penalty box that goes wide left of the target.16:42
Perez Pablo Garcia takes a corner.16:28
Giorgos Fotakis takes a shot. Blocked by Vedran Corluka.14:28
Dimitris Salpingidis concedes a free kick for a foul on Luka Modric. Luka Modric restarts play with the free kick.12:59
Georgios Georgiadis provided the assist for the goal.12:59 Goal scored
Goal! - Stefanos Athanasiadis - Tottenham 0 - 2 PAOK Stefanos Athanasiadis grabs a goal from deep inside the penalty box low into the middle of the goal. Tottenham 0-2 PAOK Salonika.11:07
Outswinging corner taken by Aaron Lennon from the right by-line played to the near post.9:49
Foul by Danny Rose on Dimitris Salpingidis, free kick awarded. Free kick taken by Oeliton Etto.8:36
A cross is delivered by Luka Modric, clearance made by Perez Pablo Garcia.8:01
Luka Modric takes a inswinging corner.6:58
Free kick awarded for an unfair challenge on Danny Rose by Dimitris Salpingidis. Free kick taken by Danny Rose.6:40
Stefanos Athanasiadis takes a shot. Heurelho Gomes makes a comfortable save.5:14
Georgios Georgiadis provided the assist for the goal.5:14 Goal scored
Goal! - Dimitris Salpingidis - Tottenham 0 - 1 PAOK Dimitris Salpingidis finds the net with a headed goal from inside the box. Tottenham 0-1 PAOK Salonika.5:14
Georgios Georgiadis delivers the ball,3:50
Konstantinos Stafylidis fouled by Aaron Lennon, the ref awards a free kick. Kostas Chalkias restarts play with the free kick.0:00
The referee gets the game underway.
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