Spurs’ run to last season’s final was littered with great escapes and last-ditch turnarounds but their group stage this term looked like getting off to a winning start in Athens.
It confirmed boss Mauricio Pochettino’s assertion that Spurs would not be among the favourites to win this season’s competition and though the draw means they will still be expected to get out of this group – which also features Bayern Munich and Red Star Belgrade – with relative ease.
They could have laid down a big marker towards that goal, but instead will be heading back to London on the back of a difficult night and with a 12.30pm kick-off on Saturday at Leicester to prepare for.
Spurs only had to look at the stats to know how tough this was going to be for them as they were visiting the home of a side who had lost once in their own backyard since September last year.
It is easy to see why as, backed by a vociferous support who were hardly welcoming to their visitors, the Greek side were quickly on the front foot and Spurs endured a torrid opening 20 minutes.
They had an early warning after only five minutes when Podence got in down the left, but his shot was weak and straight at Lloris.
Lloris was beaten in the 18th minute as a sweeping Olympiacos move saw Omar Elabdellaoui’s cross find Miguel Angel Guerrero, but his volley smashed into a post and Guilherme’s follow-up went over the crossbar.
Spurs were desperate for a foothold and they were handed the perfect way to change the course of the game in the 26th minute when Kane jinked into the penalty area and was clumsily tripped by Yassine Meriah.
Once VAR verified the decision, Kane showed nerves of steel as amid a deafening chorus of jeers and whistles he dispatched the spot-kick down the middle, putting his miss from 12 yards for England last week firmly behind him.
That proved just the tonic for Spurs and they doubled the lead only four minutes later.
Ben Davies intercepted the ball and teed up Moura, who fired a fierce drive into the top corner from the edge of the area.
If Spurs had any notion that the game was won then they had a rude awakening as Olympiacos opened the door on a comeback a minute before the break.
Podence played a neat one-two with Valbuena and when he got the ball back, he drilled a low finish into the bottom corner.
Then Pedro Martins’ side, after seeing Spurs have a Dele Alli goal disallowed, barged that door down when they were awarded a 53rd-minute penalty.
Jan Vertonghen carelessly caught Valbuena and the Frenchman sent his former international team-mate Lloris the wrong way from the spot to level it up at 2-2.
Spurs had made a mess of their lead – the second time they had squandered such an advantage in three games – but did at least try to recover the situation and a fine chance fell to Alli midway through the second half.
A ricochet saw the England international burst through on goal but his shot from a narrow angle was saved by Jose Sa, with Kane begging for a tap-in in the centre.
For all of Tottenham’s struggles in the match they were at least the ones pushing for victory and Kane was again fuming when Erik Lamela opted to shoot when he might have squared it.