Pompey gave Bolton Wanderers a real scare before going down 2-0 in their maiden FA Cup final on April 27, 1929.
The Blues had shocked the country by making it to Wembley during a difficult campaign.
Jack Tinn’s side finished just one spot above the First Division relegation zone, while opponents Bolton were comfortable in mid-table.
The Trotters, who lifted the Cup in 1923 and 1926, came into the match as overwhelming favourites.
But when the game kicked off in front of a crowd of 92,576 fans, it was Pompey who took the early initiative.
The only disappointment for the Blues was that Jack Weddle – and his famously fierce shot – was shackled by Bolton full-back Alex Finney.
And the first half ended goalless, despite the Fratton Park outfit catching the eye.
Upon their return, Bolton discovered a new sense of urgency and began to apply to pressure to the Blues.
Pompey goalkeeper Jock Gilfillan found himself under attack from all angles as George Gibson, Jim McClelland and Harold Blackmore all tried and failed to break the deadlock.
With Wanderers in command, Blues left-back Thomas Bell picked up a painful-looking knock – forcing him to switch to outside-left.
And it was a move which severely hampered the balance of Tinn’s side.
Pompey continued to cling on but with just 11 minutes remaining Billy Butler managed to wriggle through – cutting inside before firing past a helpless Gilfillan to make it 1-0.
Desperate to get back into the contest, the Blues went on the offensive.
But on 87 minutes Butler’s perfectly-placed cross found Blackmore and he blasted into the net before Gilfillan had a chance to move.
The trophy headed back up north with Bolton but it remained an historic day for Pompey – the first of five FA Cup final appearances.
The Blues had beaten Charlton Athletic, Bradford City, Chelsea, West Ham and Aston Villa on the road to Wembley.
Pompey: Jock Gilfillan, Alec Mackie, Thomas Bell, Jimmy Nichol, Johnny McIlwaine, David Thackeray, Fred Forward, Jack Smith, Jack Weddle, David Watson, Fred Cook
Bolton Wanderers: Dick Pym, Bob Haworth, Alex Finney, Fred Kean, Jimmy Seddon, Harry Nuttall, Billy Butler, Jim McClelland, Harold Blackmore, George Gibson, Willie Cook