Boro have been handed an Emirates FA Cup third round home tie against Tottenham Hotspur.
Tottenham, Champions League finalists last season, are currently fifth in the Premier League and are now managed by Jose Mourinho.
The Riverside clash will see Jonathan Woodgate and Robbie Keane face another of their former clubs.
The tie will be played over the weekend of January 4 2020.
Ticket information will be available in due course.