Tottenham, Celtic and Birmingham all lost their Europa League games leaving their progression in the competition hanging by a thread. Spurs went down 2-1 at home to 10-man PAOK Salonika on a controversial night at White Hart Lane.
The home side went two goals down, pulled a goal back and then thought they had equalised through Jermain Defoe in the second half, but referee Bas Nijhuis penalised the striker for a foul.
Tottenham now need to win against Shamrock Rovers in Ireland in a fortnight's time and hope PAOK overcome Rubin Kazan in Thessaloniki.
Birmingham missed a first-half penalty then conceded the only goal of the game shortly after the break for a 1-0 defeat at Braga.
The Blues can still qualify if they beat Maribor at home next month.
Rubin Kazan 4-1 Shamrock Rovers, GpA Haedo Valdez Oman 12 10, 51 Natcho 36 Martins 62
Braga 1-0 Birmingham, GpH Viana 51
FC Metalist Kharkiv 4-1 Austria Vienna, GpG Devic 17 Mader 19 Lacerda Edmar 40 Gueye 60 Sosa 89
Malmo 0-0 AZ Alkmaar, GpG
NK Maribor 3-4 Club Brugge, GpH Volas 11 , 68 Donk 90 Hoefkens og51 Dirar 74 , 77 Akpala 81
Legia Warsaw 0-3 PSV Eindhoven, GpC Zewlakow og 32 Mertens pen 60 Labyad 68
Rapid Bucharest 1-3 Hapoel Tel-Aviv, GpC Deac 43 Nosa Igiebor 12 Tamuz pen 40 Toama 45
Tottenham 1-2 PAOK Salonika, GpA Modric pen 39 Salpingidis 6 Athanasiadis 13
Vorskla Poltava 1-1 FC Copenhagen, GpB N'doye og 31 N'doye 37