With Boro set to welcome The Robins to the Riverside (kick-off 7.45pm), we look back at five players to have featured for both Boro and Bristol City.
After establishing his league credentials with Swindon Town, the towering central defender racked up nearly 250 appearances in five years with Bristol City. Showing his prowess in both penalty boxes, Flint scored 16 goals in the 2014/15 season as The Robins were promoted from League One, including one at Wembley in the final of the Football League Trophy and a hat-trick in an 8-2 demolition of Walsall on the final day of the season. He was named in the PFA Team of the Year that season, and won City's Player of the Year award in the subsequent two as Lee Johnson's side cemented their place in the second tier.
George Saville was briefly a teammate of Flint's at Ashton Gate, having spent seven games on loan there from Wolves in 2015.
The midfielder-turned-pundit - now heavily involved with Boro's young loanees as part of his role as Academy Ambassador and Player Welfare Manager - had two spells out on loan during the final season of his playing career at Boro, and the second was with Bristol City. Having featured for Barnsley in the first half of the season, Maddison played seven times for The Robins as they finished ninth in the Second Division, scoring once in a 2-2 draw with Oldham.
As popular with fans at Ashton Gate as he was at the Riverside, Adomah recorded similarly consistent number of appearances with Bristol City as he did with Boro. The Ghanaian joined The Robins from Barnet in 2010 and was an instant hit, scoring 17 times in 136 games over the next three years. Moving to Boro in August 2013, he would feature 143 times and score 26 in the three years that followed before joining Aston Villa in 2016.
Knottingley-born full-back Cooper was a mainstay in Don Revie's successful Leeds side of the 60s and 70s, and was brought to Boro by one of his former teammates there, Jack Charlton. He stayed at Boro from 1975 to 1978 before moving on to Bristol City. After his initial stint with The Robins, he would cross the city divide to turn out for Bristol Rovers, also playing for Doncaster before returning to end his career at Bristol City. Cooper also holds the rare distinction of having managed both Bristol clubs.
Following Boro's Play-Off final defeat in May 2015, Tomlin left to pursue his ambition of top-flight football with AFC Bournemouth. He struggled to hold downing a starting berth with The Cherries, and eventually returned to the Championship on loan with Bristol City in January 2016. Such was the success of his time with The Robins, they opted to make the move permanent the following summer. He spent one more year at Ashton Gate before moving on to nearby Cardiff City - and although The Bluebirds earned promotion last season, Tomlin spent most of it reunited with Aitor Karanka on loan at Nottingham Forest.
Congolese-born striker Leroy Lita began his pro career with Bristol City at the turn of the century, having played youth football for Chelsea. Rising through the ranks at Ashton Gate, Lita really came to prominence in his final of three seasons with Bristol City, when he scored 29 goals for the then-League One club, prompting Championship Reading to shell out a club record £1m transfer fee. Lita's form also earned him an England Under-21 call-up, scoring on his debut against the Netherlands. Now coming to the end of a nomadic career, Lita most recently turned out for non-league Margate in 2018.
Lita is pictured above celebrating with Lee Miller, whose first club in England were Bristol City. The forward played there between 2003 and 2005, scoring 8 goals in 48 games.
Czech defender Kalas had not joined Bristol City by the time the sides last met in August, but he put pen to paper on a loan deal with the Robins less than a week later. As he was during his eighteen months on loan with Boro between 2015 and 2016, Kalas remains a Chelsea player. Now 25, Kalas followed his success on Teesside with two seasons at Fulham, where he also helped the West London side to promotion. A regular with City this season, he recently turned out for the Czech national side against England at Wembley, though it was an evening to forget for Kalas as he conceded a penalty and scored an own goal in a 5-0 defeat.
Kalas is one of a number of former Boro defenders also to turn out for Bristol City in recent years. Andre Bikey was briefly at Ashton Gate on loan from Burnley before joining Boro in 2012, Stephen McManus heading in the opposite direction the same season. Matthew Bates also joined the South West club in 2012 after years of battling injuries at Boro, but was limited to fewer than 20 first team appearances before moving to Bradford City. Gary O'Neil is another to enjoy a spell in Robins colours between 2016 and 2018.
Aussie midfielder Luke Wilkshire was a product of Boro's youth system having moved to these shores in to sign for the Teesside club in 1998. Struggling to make an impression at Premier League Boro, Wilshire moved to Bristol City in search of first team football, and became a mainstay for the second-tier side over the next three seasons, scoring 18 goals in 124 games. His career since has taken Wilkshire all over Europe, playing for teams such as Twente, Dynamo Moscow and Feyenoord, more recently returning to his homeland with Sydney FC and hometown club Wollongong Wolves, where he is now manager.