The peak of this era was winning the FA Cup in 2008 and then participating in the UEFA Cup, in which exactly 16 years ago on November 27th, Portsmouth faced the famous Italian side AC Milan. But not long after, a dark period came when Pompey almost disappeared off the footballing map.
Ending the trophy drought
In the 2007-08 season, Portsmouth were an established Premier League club, having been promoted to the top flight in England in 2003.
In their first few Premier League seasons, Pompey were more of a club that fought to avoid relegation, but they had finished in ninth in 2006-07.
The team from the south coast achieved even greater success in the aforementioned FA Cup a season later, which they won, thus securing a major trophy for the club after almost six decades without one.
On their way to the final, Pompey eliminated, among others, Manchester United. Their opponent in the final was Cardiff City, then in the Championship.
Portsmouth defeated the Welsh side 1-0 and won the FA Cup for the second time in the club's history - their first triumph was achieved in 1939.
Nwankwo Kanu scored the decisive goal of the final at Wembley. The Nigerian striker, who previously made his name with Arsenal, was one of the biggest stars of the Portsmouth team at the time.
Manager Harry Redknapp also had other great players in his squad. In goal was the experienced David James, the cornerstone of the defence and the captain of the team was Sol Campbell, and Glen Johnson played at right back.
The midfield consisted of African greats Papa Bouba Diop and Sulley Muntari as well as Lassana Diarra and Niko Kranjcar, and alongside Nwankwo Kanu was Jermain Defoe in attack.
Just seconds away
Portsmouth's squad underwent several changes before the 2008-09 season, with Ghanaian Muntari leaving the club to join Inter while lanky striker Peter Crouch and French defender Younes Kaboul were brought in.
Pompey were preparing for their first-ever participation in a European competition in the club's history (and we can reveal that it was also their last participation to date).
The UEFA Cup group stage then had a format of groups consisting of five clubs playing against each other only once. The highlight for Portsmouth was the match against AC Milan, which featured the holder of the 2007 Ballon d'Or and the UEFA Club Footballer of the Year, Kaka. Pompey played this big match at home, at Fratton Park.
The crowd who filled a sold-out Fratton Park saw an outstanding match. The first half ended goalless but Pompey had a great start in the second. They took a 2-0 lead with goals from Kaboul and Kanu while Crouch missed three good chances.
In the 84th minute though, Ronaldinho scored from a free kick for Milan, and sadly for the home side, Filippo Inzaghi equalised in the second minute of injury time.
The draw with AC Milan was Portsmouth's second match in the UEFA Cup group stage after they had lost their first match in Braga.
Then, they lost to Wolfsburg in Germany and their only win came at home against Heerenveen from the Netherlands. A total of four points was not enough to get out of the group. The European dream was over, but not long after, Portsmouth faced much bigger problems.
On the brink
Portsmouth's seven-year stay in the Premier League ended in 2009-10 with relegation, but that was only a signal of even deeper troubles.
The club entered financial administration twice and were relegated three times. Later, in 2013, Portsmouth were purchased and saved by the Pompey Supporters Trust.
Pompey would begin to recover financially and won the League Two (the fourth tier of the English football league system) title in 2016-17 and the League One title in 2023-24. Thanks to this, Pompey are back in the Championship.
In terms of titles from various league competitions, Portsmouth managed to win also the second-highest division in 2003 but they even won the title in the first division twice in a row in 1949 and 1950.
This makes Portsmouth one of only five English football clubs to have been champions of all four tiers of the professional English football pyramid. Will we ever see this unique club on the highest stage in the Premier League again?