Harry Kane's brace helped Tottenham Hotspur to seal their spot in the last 16 of the Champions League.
José Mourinho's home debut began on the back foot but his Lilywhite's clawed back the victory after conceding two early goals.
Story of the game
Youssef El-Arabi had clearly not read the script as he gave the visitors an early lead with a superb left-footed strike from outside the box.
Danny Rose's clearance left a lot to be admired and Frenchman made the Lilywhite's pay for their mistakes after a promising opening five minutes for the Greek side.
Rúben Semedo doubled the Greek side's lead after nudging in from a corner which trickled straight through the Spurs defence.
Mourinho's home debut was not going to plan with the other Portuguese manager enjoying the action.
The next goal was looking increasingly likely to go in the favour of Olympiacos forcing Mourinho to introduce Christian Eriksen after just 25 minutes.
Harry Kane's free-kick from 20-yards marked the home side's best attempt on goal and the Englishman failed to hit the target - summing up a poor first half for Mourinho's men.
Seconds before the interval, Spurs were gifted a goal through a miss-kick from Yassine Meriah left Dele Alli an open goal to aim at.
A lifeline for Spurs - an undeserved one but still a glimmer of hope on a night where a win would see them through to the final 16.
Shortly after the break, Kane drew the game level with a sweet finish from inside the box.
Quick thinking from Lucas Moura saw the Brazillian race clear before switching the ball into the feet of Kane.
Serge Aurier's venomous half-volley cannoned Spurs into the lead with 20-minutes remaining.
It was a strike even Harry Kane would have been proud of - marking a strong start under the new boss for the Ivorian.
And it was Kane who wrapped the game up and his header made him the quickest player to reach 20 UCL goals (24 games).
Takeaways from the game
Fighting spirit but defensive woes
The first half was one to forget for Spurs. Defensively inept and lacking ideas going forward.
The Spurs backline once again showed cause for concern after the visitors earned themselves an early two-goal lead.
For the second time in three days, Paulo Gazzaniga found himself picking the ball out of his net on two occasions.
However, Kane's early strike in the second half gave the side a new lease of life which saw them go on to snatch the victory.
It seems the 'old Dele' is on the cusp of returning to his best.
The 23-year-old impressed on Saturday against West Ham and tonight gave Spurs the goal which started the comeback but it was his attitude on the pitch which really stood out.
Confident, positive and most of all looking like he is enjoying his football this could be the start of Dele's return to form.