Jose Mourinho and his Tottenham Hotspur charges are away in their first involvement in the competition this season.
Jose Mourinho's charges will head to the Riverside Stadium on the first weekend of January to face Boro, who are currently struggling in the Championship.
Tottenham cult hero Jonathan Woodgate is currently in charge at the club - with Robbie Keane as assistant - but he is currently under pressure and being slammed by sections of the Boro fanbase due to the club's poor form.
Boro were beaten 4-0 by Leeds United last time out, a result which meant just one win in 11 for Woodgate, whose side currently sits 20th in the table, just one point outside the bottom three.
In contrast, Tottenham have been flying since Mourinho replaced Mauricio Pochettino at the helm of Spurs, with three wins in a row - albeit with two goals shipped in each of these games.
However, an away trip - and a fairly long one at that - not to mention memories of the Colchester loss in the League Cup made some fans a bit nervous, even if on paper they will be heavy favourites.
Here is what some Tottenham fans said on social media after the draw was announced by the Spurs channel:
Thank god it isn't Colchester— George (@georgespursvlog) 2 December 2019
Yet another away cup draw— Joe (@JblincoTHFC) 2 December 2019
ffs if we lose i’m actually done— Jacob Marley (@jacobmarley24) 2 December 2019
Ffs wanted a home game— MV (@VamosYids) 2 December 2019
Keano and Woody ... if they are still in charge by then— josh graham (@spurs9019) 2 December 2019
Ffs another Colchester— Shakur (@Ace_THFC) 2 December 2019
Now please don’t Spurs it up like last time— |R|S (@zerofoxgiven75) 2 December 2019
Oh— Nxombele28_= W (@Nxombele28_) 2 December 2019
Are we ever at home— Prem side 1992-2020 (@THFC3002) 2 December 2019
Third round ties will take place across the weekend of Friday 3 January to Monday 6 January, 2020.
Have something to tell us about this article?