Lucas Moura equalised to salvage the tie, but Jose Mourinho will demand a much better display on home soil.
RadioTimes.com has rounded up everything you need to know about how to watch the Tottenham v Middlesbrough game on TV and online.
What time is Tottenham v Middlesbrough?
Tottenham v Middlesbrough will kick off at 8:05pm on Tuesday 14th January 2020.
How to watch Tottenham v Middlesbrough on TV and live stream
Fans can tune in to watch the game for free on BBC1 from 8:00pm.
You can also live stream the match via BBC iPlayer on a range of devices including laptops, smartphones and tablets.
Where is the game being played?
The game is being played at the new Tottenham Hotspur Stadium, which opened on 3rd April 2019. It replaces Tottenham's old home of White Hart Lane and has an impressive capacity of 62,303, making it one of the larger club ground in England.
When did Jose Mourinho become Spurs manager?
Jose Mourinho was named as the Tottenham Hotspur head coach on 20th November 2019, replacing Mauricio Pochettino who was sacked the previous day after more than five years at the helm of the club following what Spurs Chairman Daniel Levy described as an "extremely disappointing" start to the 2019/20 domestic season.
Why is Harry Kane not playing?
The England captain and Spurs number nine Harry Kane won't be playing in this match because he's injured after rupturing a tendon in his left hamstring during a Premier League game with Southampton.
According to Tottenham Hotspur, the star striker is expected to undergo surgery but may not return to training until April.
At this stage it is not clear whether he will take part in any further matches for Spurs this season, or whether he will be recovered in time to play for England in Euro 2020 this summer.
How to buy Tottenham v Middlesbrough tickets
Tickets are still available for the game via the Ticketmaster website.
Check out the latest deals on Tottenham v Middlesbrough tickets
Tottenham have all of the tools to go on and win the competition, the question is whether they want to.
Too often Spurs stars look a yard off the pace, overly casual and lacking intensity.
They should find a way through this one, but a drastic attitude shift will be required for Mourinho’s men to mark this season with any kind of success.
Prediction: Tottenham 2-0 Middlesbrough
