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.
1. Albert Adomah
One of Boro's promotion winners from the 2015/16 season. The Teessiders signed Adomah from Bristol City in 2013 and the winger, who has since joined Nottingham Forest, remains a popular figure at both clubs. Photo: Richard Sellers
2. Neil Maddison
The BBC Tees pundit remains heavily involved with Boro's youth set-up in his role as academy ambassador and player welfare manager. During his playing days, Maddison spent four years at Boro and had a brief loan spell at Bristol City. Photo: Clive Mason
3. Lee Tomlin
After helping Boro reach the Championship play-off final in 2015, Tomlin left Teesside for Bournemouth. He then signed for City permanently following a loan move to Ashton Gate and has since returned to Cardiff after spells at Nottingham Forest and Peterborough. Photo: Jan Kruger
4. Tomas Kalas
The Czech defender is set to miss this weekend's clash after suffering a hamstring injury. Kalas signed for City permanently this summer following several spells out on loan from Chelsea, including two at Boro. Photo: Alex Davidson