Ahead of our semi-final clash at the Memorial Stadium, we take a look at three players who made a contribution to the history of the two clubs.
Bristol-born Marcus Stewart started his career at Bristol Rovers as a 19-year-old making 207 appearances and scoring 79 goals between 1991 and 1995. His second season saw Bristol Rovers make their last appearance in the second tier of English football.
Stewart’s form at The Pirates over those five years were enough to see a move to join ex-Sunderland goalkeeper Tony Norman at Huddersfield Town in 1995, signing for a club record £1.2 million.
After almost four years, 160 appearances and 68 goals at The Terriers, another club record fee was shelled out when Stewart moved to Ipswich Town in February 2000 for £2.5 million. Promotion to the Premier League was achieved three months later via the play-offs.
In 2000/01, Ipswich would go on to finish 5th in the Premier League, qualifying for what was then the UEFA cup, and Stewart would score 21 goals in all competitions.
A year later Ipswich Town were relegated and he signed for the lads for a reported £3.25 million, going on to score 53 goals in 119 games between 2002 and 2005.
After spells at Bristol City, Preston North End, Yeovil Town and Exeter City he hung up his boots in the summer of 2011 immediately moving into a first team coach role at Exeter City.
This was followed a year later with a return to Bristol Rovers as a development coach then moving to the role of assistant manager in 2013. He left the club by mutual consent in December 2018 along with manager Darrell Clarke.
Paul Hardyman signed for his home town club Portsmouth on the same day as Kevin Ball and would go on to make over 100 appearances for Portsmouth between 1983 and 1989.
He was Denis Smith’s only signing during the summer of 1989, signing on the dotted line for £130,000, ahead of Sunderland’s second season in the second tier that would eventually lead to promotion via the play-offs...and also via Swindon Town breaching 36 football league rules.
The play-off semi-final against Newcastle United however, would give Hardyman his most memorable moment in a Sunderland shirt. For those who this needs an explanation, it was the first-leg of the play-off semi-final against our nearest and dearest at a packed Roker Park, 0-0, and then a penalty is awarded to Sunderland in the last minute.
As he was our regular penalty taker, Hardyman stepped up and took an uncharacteristically poor penalty which, when saved by John Burridge, was followed up by a reckless tackle by Hardyman that attempted to place the ball, and John Burridge, into orbit.
Needless to say this received a red card and has only entered folklore due to the fact we won the second-leg.
After the setback of only making the bench for the 1992 FA Cup final (replacing David Rush with twenty minutes to go), Hardyman left Sunderland that summer after making 114 appearances and scoring 12 goals, signing for Bristol Rovers for £160,000.
Over the next three years Hardyman made 67 appearances for Bristol Rovers leaving in 1995 for Wycombe Wanderers, before ending his career with Barnet in 1997.
Coaching roles have followed at Portsmouth and Watford and in July 2018 Paul Hardyman joined Southampton in an academy coaching role.
Tim Carter made his football league debut at the age of 18 for Bristol Rovers in 1985. He went on to establish himself over the next two years and made 47 appearances for The Pirates before Denis Smith signed him on Christmas Eve 1987 for an initial £35,000 increasing to £50,000 based on appearances.
Despite spending the majority of his time as cover for Iain Hesford or Tony Norman, or out on loan to Carlisle United, Bristol City and Birmingham City, Carter went on to make 50 appearances for Sunderland before joining Hartlepool United in 1992.
From Hartlepool United, Carter went on to play for Millwall, Blackpool, Oxford United (reuniting with Denis Smith) and Halifax Town before retiring in 1999.
He returned to Sunderland in the roles of first team and academy goalkeeper coach whilst also holding the position of goalkeeper coach to the Estonia national team.
Tim Carter tragically committed suicide at the age of 40, his body was found in the Stretford area of Manchester in 2008.