Ahead of Saturday’s league meeting, we’ve picked out nine players who have represented both clubs and take a look at what has happened in their careers since. Scroll down and flick through our picture gallery to see the full list.
5. Gary O'Neil
The midfielder made over 100 appearances for Boro between 2007 and 2011 before leaving for West Ham. Now 36, O'Neil has gone on to represent QPR, Norwich, Bristol City and Bolton. | 2008 Getty Images Photo: Alex Livesey
6. Matthew Bates
A player whose career was blighted by injuries. Even so, Bates made over 100 appearances for Boro after progressing through the youth ranks, before signing for Bristol City in 2012. The defender made 13 appearances for the Robins. | 2011 Getty Images Photo: Michael Steele
7. Andre Bikey
The well-travelled centre-back spent one season at Boro after joining the club under Tony Mowbray. Before that, he made a handful of appearances for City during a loan spell from Burnley. | 2012 Getty Images Photo: Stu Forster