Spurs open their Champions League campaign with an away trip to the San Siro where Inter Milan await.
Both sides suffered defeats in their domestic games over the weekend and will be looking to respond in style.
But it is no wins in two for Mauricio Pochettino's side and the Lilywhites host a list of injuries to some of their key players.
Last time out
Similarly to this season's Champions League, last year Spurs were drawn the proclaimed 'group of death'.
This year, Spurs will face Barcelona, PSV and Inter in their quest to progress from the group stages and at least match last years' round of 16 achievement.
However, Pochettino's side tasted defeat over two legs against Juventus to be dumped out of the 2017/18 competition.
The Lilywhites have a mixed bag of results in recent trips to the San Siro, in 2010 a 4-3 defeat was overshadowed by a miraculous late hat-trick from Gareth Bale.
In 2011, Spurs beat AC Milan 1-0 thanks to a Peter Crouch goal in their away leg of a round of 16 tie against the Italian giants.
Tottenham have tasted back-to-back defeats in the Premier League against Watford and Liverpool.
Much like Spurs, Inter suffered a home loss on the weekend to Parma in a narrow 1-0 defeat.
Both sides will be looking to bounce back in style but Pochettino will be looking to avoid a hat-trick of defeats.
With trips to Barcelona and PSV coming up a defeat for Spurs could prove costly in what seems to be one of the most competitive groups this campaign.
Spurs are set to travel without captain Hugo Lloris who missed Saturday's defeat to Liverpool due to a thigh injury.
Moreover, Dele Alli is also unlikely to travel with the side after picking up a knock during his time with the England side.
However, Heung-min Son will travel after his return from national duty with South Korea in their Asian Games triumph.
As for Inter, their only injury concern is to defender Sime Vrsaljko who picked up a knee injury during the international break.