Monday night sees Arsenal return to Fratton Park for the first time in 11 years to take on Portsmouth.
For much of the noughties, these two sides met as Portsmouth were promoted to the Premier League for the first time in their history.
However, after a dramatic fall from grace for the south-coast side, the fixture has remained consigned to the annals of history.
We look at the rise and fall of Pompey as they prepare for their FA Cup clash, one of their most high-profile fixtures since becoming the first ever Premier League team to go into administration.
In the late ‘90s and early ‘00s, Pompey were a team mired in mediocrity, after a succession of average owners, poor teams and uninspiring managers.
That all changed with the hiring of Harry Redknapp, initially as director of football and then manager. With trusty sidekick Jim Smith joining him in the dugout, Redknapp built a team of young talent and a sprinkling of superstardom.
With Paul Merson pulling the strings in midfield and Svetoslav Todorov bagging 26 goals, the Blues won the league comfortably, finishing 18 points clear of third place.
Pompey’s first season in the Premier League was a resounding success and actually coincided with Arsenal’s Invincible season. Both league fixtures between the sides ended 1-1, with a questionable penalty awarded to Arsenal at Highbury salvaging their unbeaten status.
After some years of mediocrity in the highest division, Redknapp returned to Fratton Park to lead the great escape, which led to arguably Portsmouth’s finest footballing period in living memory.
The 2007/8 season will mark the peak of Pompey’s football powers in the memories of many fans.
A star-studded team of internationals, including David James, Sol Campbell, Jermain Defoe, Sulley Muntari, Glen Johnson and Lassana Diarra took Portsmouth to the 2008 FA Cup final, triumphing 1-0 against a spirited Cardiff City.
It was the side’s first FA Cup win since 1939, and just their second ever. It also saw Pompey qualify for the 2008/9 UEFA Cup.
In one of the biggest nights in Pompey history, one of football’s biggest giants came to Fratton Park.
AC Milan, boasting the likes of Kaka, Ronaldinho, Clarence Seedorf and Andriy Shevchenko among their ranks, struggled mightily against Tony Adams’ side, eventually clawing back a 2-2 draw after being 2-0 down. However, from there it was all downhill for Adams and Portsmouth.
The UEFA Cup added a sheen to a difficult season, as financial trouble started to rear its head. After the unexpected FA Cup success, owner Alexandre Gaydamak experienced some business struggles, and transfer targets quickly shifted. After being linked with Yaya Toure and Thiago Motta, Pompey ended up signing Hayden Mullins.
It was the beginning of a dramatic fall from grace for the two-times FA Cup winners, as they suffered the ignominy just a year later of being the first ever Premier League team to suffer administration, leading to the deduction of nine points and certain relegation.
Between that fixture against AC Milan and their lowest point, Pompey had six owners, of which two have since been imprisoned, three relegations and two administrations before eventually bottoming out as a mid-table League Two team.
This all happened within the space of five years. The team of superstars was dismantled to pay off debts, the club had an incredible amount of turnover, and was forced to rebuild from the very bottom of the Football League.
However, crucially, the team was now fan-owned, debt-free, and could start its rise again.
Pompey hired Paul Cook as manager in 2015, and quickly established themselves as one of the better teams in League Two.
His first season saw the Blues lose in the playoff semi-final, before winning an improbable league title in 2016. After Cook resigned, Portsmouth, under new ownership from the Tornante Company, led by former Disney CEO Michael Eisner, went into the League One season with Kenny Jackett at the helm.
Jackett has improved the side year on year and is currently in his third season at the helm. Currently third in the league with 10 games to go, Pompey are also set to defend their EFL Trophy crown at Wembley next month, while also being unbeaten at home in the league since April.
While they aren’t quite the heady days of 2008, under sensible ownership and a solid manager, Portsmouth will approach the Arsenal fixture with a sense of optimism, especially given their cup record under Jackett.