Tottenham Hotspur were booed off the pitch at half-time of their Champions League clash against AC Milan on Wednesday night.
The north Londoners were trailing 2-0 at the break after a poor first-half performance, with Zlatan Ibrahimovic and Rafael Leao scoring for the Italian side.
Spurs had started the game brightly, with Harry Kane and Son Heung-min both having chances to open the scoring, but they were unable to take them and were punished by Milan.
Ibrahimovic opened the scoring in the 15th minute, heading home from a corner, before Leao doubled the lead just before the break.
The home fans were clearly unhappy with the performance of their team and made their feelings known as the players trudged off the pitch at the break.
The second half was a much improved performance from Spurs, with Kane and Son both going close to reducing the deficit, but they were unable to find a way past Milan goalkeeper Gianluigi Donnarumma.
The result leaves Spurs with a mountain to climb if they are to progress to the last 16 of the competition, with the second leg in Milan in three weeks’ time.
It was a disappointing night for Spurs, who had been hoping to build on their impressive win over Burnley at the weekend, but they will need to improve significantly if they are to have any chance of progressing in the competition.