26 great photos of Portsmouth’s glorious Wembley triumphs - and heartbreaking final defeats

POMPEY sealed a return to Wembley after beating Bury in the semi-final of the Checkatrade Trophy last night.

The Blues will be returning to the famous stadium for the first time since the 2010 FA Cup final loss. To get fans even more excited before you walk down Wembley Way at the end of March, we’ve looked through the archives and found pictures from Pompey’s previous trips to the home of English football. 

Pompey's triumphs and defeats at Wembleyplaceholder image
Pompey's triumphs and defeats at Wembley
Supporters arrive in London for the FA Cup final between Bolton Wanderers and Portsmouth at Wembley in April 1929. Pompey fell to a 2-0 defeat on the day.placeholder image
Supporters arrive in London for the FA Cup final between Bolton Wanderers and Portsmouth at Wembley in April 1929. Pompey fell to a 2-0 defeat on the day.
Pompey fans head to Wembley by bus for either the 1929 or 1934 FA cup final. With the girls wearing their best hats and the men with neckwear.placeholder image
Pompey fans head to Wembley by bus for either the 1929 or 1934 FA cup final. With the girls wearing their best hats and the men with neckwear.
Portsmouth supporter wearing a rosette and holding a model FA Cup arrives in London for the FA Cup final against Bolton Wanderers at Wembley in 1929.placeholder image
Portsmouth supporter wearing a rosette and holding a model FA Cup arrives in London for the FA Cup final against Bolton Wanderers at Wembley in 1929.
Pompey supporter decked in gear cheering the team on in Trafalgar Square before their FA Cup Final trophy over Wolverhampton Wanderers in April 1929.placeholder image
Pompey supporter decked in gear cheering the team on in Trafalgar Square before their FA Cup Final trophy over Wolverhampton Wanderers in April 1929.
James de Mellow from Rowlands Castle was one of many Pompey fans who made their way up Wembley Way for the 2008 FA Cup Final.placeholder image
James de Mellow from Rowlands Castle was one of many Pompey fans who made their way up Wembley Way for the 2008 FA Cup Final.
Plenty of fans made their way up to Wembley from the South Coast for the 2008 FA Cup final.placeholder image
Plenty of fans made their way up to Wembley from the South Coast for the 2008 FA Cup final.
Portsmouth fans pack into Wembley stadium for the 2008 FA Cup Final against Cardiff City.placeholder image
Portsmouth fans pack into Wembley stadium for the 2008 FA Cup Final against Cardiff City.
Pompey fans waving flags at Wembley during 2008 FA Cup final.placeholder image
Pompey fans waving flags at Wembley during 2008 FA Cup final.
Young Pompey fans inside celebrate during the 2008 Fa Cup final at Wembley.placeholder image
Young Pompey fans inside celebrate during the 2008 Fa Cup final at Wembley.
Pompey fans cheer on the Blues during the 2008 FA Cup Final at Wembley Stadium.placeholder image
Pompey fans cheer on the Blues during the 2008 FA Cup Final at Wembley Stadium.
Portsmouth's Nwankwo Kanu scores the only and winning goal in 2008 FA Cup finalplaceholder image
Portsmouth's Nwankwo Kanu scores the only and winning goal in 2008 FA Cup final
Pedro Mendes and Lassana Diarra celebrate with the FA Cup after Pompey beat Cardiff.placeholder image
Pedro Mendes and Lassana Diarra celebrate with the FA Cup after Pompey beat Cardiff.
News you can trust since 1877
Follow us
© 2026 Iconic Media Group Ltd. All rights reserved.Cookie SettingsTerms and ConditionsPrivacy notice