The fixtures are coming thick and fast for Tottenham, who face a Champions League trip to AC Milan just days after falling to a 4-1 defeat at Leicester in the Premier League.
Antonio Conte's team topped their group, with Eintracht Frankfurt finishing second to join them in the round of 16. While Frankfurt are set to take on in-form Napoli, Spurs' task sees them paired with last season's Serie A champions Milan.
The Rossoneri made it into the knockout stages after finishing second in their group behind Chelsea. The Blues were the only team to beat Stefano Pioli's men, who comfortably won a deciding final group game against Red Bull Salzburg in November.
Spurs boss Conte has returned to work after gallbladder surgery, but the loss at the King Power Stadium is far from the perfect preparation. Rodrigo Bentancur gave the visitors an early lead, but it was wiped out as Papy Mendy, James Maddison, Kelechi Iheanacho and Harvey Barnes all found the net.
Worse was yet to come for Spurs, with goalscorer Bentancur out for an estimated six months with a knee injury. With Yves Bissouma already sidelined and Pierre-Emile Hojberg suspended, a makeshift midfield pairing of Pape Sarr and Oliver Skipp is expected to take to the field at the San Siro.
Club captain Hugo Lloris will also be missing through injury, with summer signing Fraser Forster deputising. It will be a first Champions League outing for veteran goalkeeper Forster since a 6-1 defeat for Celtic at Barcelona in 2013.
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"We believe we’re equal to Tottenham," Milan boss Stefano Pioli said in. Winning the Champions League is a dream but it’s useless to think about it now. A week ago, they beat Manchester City, but we don’t come in better or worse than them. It will be a big game that we will have to play well."
These two teams have met at this stage of the Champions League once before. On that occasion, Peter Crouch scored Spurs' winner at the San Siro before a goalless draw in London sent the Premier League side through.
When is the match?
AC Milan v Tottenham Hotspur will take place at the San Siro on February 14. Kick-off is at 8:00pm GMT.
How can I watch it?
In the UK, viewers will be able to watch Milan v Spurs on BT Sport 1. Pre-match build-up will begin an hour before kick-off, at 7:00pm GMT.
BT Sport subscribers will also be able to watch the game via the BT Sport website or app.
Match odds from Betfred
AC Milan 6/4
Draw 11/5
Tottenham 15/8
*odds subject to change
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