London, England – Greek side PAOK earned a shock victory at 1, to clinch a two finish in Group A and secure a spot in the next round of the Europa League.
Spurs found themselves down by two goals inside the opening 14 minutes.
Dimitrios Salpigidis got PAOK off to a dream start when he nodded his side in front in the sixth minute, and Stefanos Athanasiadis extended the lead eight minutes later when he slid in at the back post to stuff home a low cross inside the six-yard box.
Tottenham received a lifeline just before halftime when Kostas Stafylidis was sent off for handling the ball and denying a would-be goal.
Luka Modric stepped up and smashed home the ensuing penalty to cut the deficit in half.
Spurs were controversially denied a goal in the second half after Jermain Defoe collided with a PAOK defender on the goal line. Play continued and Defoe eventually found the net, but the referee pulled play back after his assistants cited the English striker for an infraction.
With the unlikely win, PAOK moves to the top of Group A with just one match remaining, setting the pace with 11 points.
Rubin Kazan dismantled Shamrock Rovers, 4-1, in Group A's other Wednesday fixture to move into second place with ten points. Rubin will advance from the group with just a point from its final match at PAOK on Dec. 15.
Tottenham sits third with seven points and must defeat Shamrock on Dec. 15 in order to advance, while hoping that PAOK will still show up to beat Rubin Kazan despite being assured qualification.
In Group B, Standard Liege booked a place in the next round with a 2-0 win over Hannover, and Dame N'Doye made amends for his own goal in the 31st minute by scoring at the other end six minutes later, helping Copenhagen salvage a 1-1 draw with Vorskla Poltava.
In Group C, PSV Eindhoven edged ten-man Legia Warsaw, 3-0, with both sides already qualified for the next round, and Hapoel Tel Aviv claimed its first win of the competition with a 3-1 defeat of Rapid Bucharest.
In Group G, Metalist Kharkiv clinched a spot in the next round with a comfortable 4-1 win over Austria Vienna, while Malmo earned its first point in this season's Europa League campaign in a 0-0 home draw with AZ Alkmaar.
In Group H, Club Brugge overturned a three-goal deficit with just 16 minutes remaining to earn a 4-3 victory over Maribor, and Birmingham City was left to rue a missed penalty from Nikola Zigic as Hugo Viana handed Braga a 1-0 home win.