The two sides last met in 2016-17, which was Boro’s only season in the Premier League in the last decade. Spurs won 1-2 on the road and 1-0 at home with a brace by Son Heung-Min at Riverside Stadium and a penalty by Harry Kane during the return fixture.
Of the draw, the biggest highlight was league-leader Liverpool drawing rival Everton for a Merseyside derby. Manchester United will face a Wolves side that currently sits equal to Spurs in points. Meanwhile, Arsenal and Chelsea drew Leeds United and Nottingham Forest, respectively, who both sit in the top four of the Championship table.
The time and date of Tottenham’s fixture have not yet been announced, but it is scheduled to be played sometime during the first week of January. The full draw is listed below: