Tottenham sacrificed an early lead as their Europa League campaign suffered a blow with defeat to Anderlecht.
Head coach Mauricio Pochettino fielded a strong side in Brussels and brought Harry Kane off the bench with the scores level after initially resting the England striker as he suffered a knock against Liverpool.
Things looked to be going smoothly for the Premier League side as Christian Eriksen scored early on after a positive start – but after a number of missed chances the hosts levelled through Guillaume Gillet’s volley, with Stefano Okaka striking late on to secure a 2-1 win for the Belgian side.
Tottenham drew here in the first leg of their UEFA Cup final success over Anderlecht in 1984 and were held when the sides were drawn together in the group stages back in 2007.
It is testament to how far Kane has come that he was rested here given that 12 months ago this was the only competition in which he was being given a chance to make his name.
In his absence Pochettino named Clinton Njie as his lone striker, handing his summer recruit his maiden start for Spurs, who also included Belgium international trio Jan Vertonghen, Toby Alderweireld and Mousa Dembele in their starting line-up.
The game started at a frenetic pace as Hugo Lloris tipped Imoh Ezekiel’s early cross behind for a corner before Eriksen’s tame effort marked Tottenham’s first attempt of the night.
The Danish playmaker made no mistake soon after as he collected possession following a fortuitous rebound and tucked the ball past Silvio Proto to put Spurs ahead inside five minutes.
Anderlecht could not stop Eriksen running the game and he came close to adding a second with a free-kick that deflected inches wide of Proto’s goal with the hosts’ skipper stranded.
Next up, Eriksen turned his hand to trying to lay on the goals as he exchanged passes with Eric Dier before sliding in Erik Lamela, who should have done better when through one on one.
Despite the early threats, Tottenham were made to rue their inability to add to their lead as Gillet’s controlled volley from Steven Defour’s corner levelled the game.
In-form Okaka then stung the palms of Lloris to shake the visitors back into life with Lamela having a goal chalked out for offside on the half-hour mark following a surging run from Vertonghen.
Njie had a chance to open his account for Tottenham before the break but instead tried to pick out Eriksen, who was quickly closed down by Proto before Andros Townsend bent an effort around the post.
The second half started evenly and Pochettino turned to Kane with a little over half an hour remaining as he replaced Njie, with Dele Alli also introduced as Dembele made way.
Kane was soon involved as he held off Kara Mbodji before testing Proto as Tottenham again could not take a good chance when it presented itself.
And once more they were made to pay for that fact as substitute Frank Acheampong skipped past Kieran Trippier with ease before crossing for Okaka to sweep Anderlecht ahead.
It was the Italian’s sixth goal in as many games and the result should have been worse for Pochettino’s side as Leander Dendoncker headed over from two yards out before Lloris made a superb late stop from Dennis Praet.
The victory for Besnik Hasi’s side really opens up Group J, with both Anderlecht and Spurs now on four points from their opening three fixtures and Monaco alone at the head of the pool.