Tottenham have achieved a lot of new heights under Mauricio Pochettino, but Tuesday saw the club hit a new low in his time with the club.
Coming into their 2018-19 Champions League opener against Inter, Spurs had fallen to two straight defeats, with their 3-0 win over Manchester United followed by losses to Watford and Liverpool either side of the international break.
However, things appeared to be looking brighter for Tottenham against Inter as a second-half goal by Christian Eriksen had them up at San Siro late on.
But Mauro Icardi managed to draw Inter level with an impressive strike in the 85th minute and spoil Tottenham’s party.
Spurs could have still come away with a point, but a goal two minutes into stoppage time by Matias Vecino consigned the visitors to a tough defeat and rough start to their Champions League campaign.
It marked the first time in the Pochettino era that Spurs have lost three straight games.
The last time Tottenham lost three in a row was back in March 2014 under Tim Sherwood. Spurs were soundly defeated by Chelsea 4-0, then followed up with a 3-1 loss to Benfica in the Europa League and a 1-0 defeat to north London rivals Arsenal.
A draw with Benfica which knocked them out of Europe followed, before they got back to winning ways with a victory over Southampton - who coincidentally were managed by Pochettino.
Though the loss to Inter will hurt, it is not quite fatal to Spurs hopes of getting out of the group stage, though a tough home date against Barcelona is their next fixture in the group.
In the meantime, Spurs will look to end their winless streak on Saturday when they travel to Brighton in the Premier League.