Middlesbrough have had their fair share of signings over the years that have made a significant impact with the club, whilst others haven’t hit the heights originally set for them.
Boro are currently sat seventh in the Championship table, and will be hoping they can put together a positive run of results to mount a serious challenge for promotion into the Premier League this term.
But do you know which club Middlesbrough’s most expensive departures joined after departing the Riverside? Test your knowledge in our quiz!
Transfer fees sourced from Transfermarkt.