Pompey failed to become the first side to successfully defend the Papa John’s Trophy after losing on penalties to Salford in the Wembley final.
Ryan Williams and Ronan Curtis both missed from the spot and their League Two opponents made no mistake.
The contest had finished goalless after 120 minutes, with the Ammies controlling the first half, only for the Blues to hit back after the break.
But neither side could find a breakthrough – despite plenty of chances – and Salford kept their nerve in the shoot-out.
Kenny Jackett made two enforced changes from the side beaten by Sunderland in the league earlier in the week.
Andy Cannon and Ellis Harrison missed out with hamstring and knee injuries respectively, so in came George Byers and Jordy Hiwula.
The sides emerged to the usual pyrotechnics associated with a cup final, while the national anthem was still belted out.
But Wembley felt even more cavernous without the raucous atmosphere that usually accompanies such an occasion – albeit one that had been postponed a year due to a global pandemic.
It was Salford who settled quicker and the fourth tier side were probably left wondering how they failed to take a lead into the interval.
An early – and fierce – long-range strike from James Wilson had to be beaten away by a diving Craig MacGillivray.
Williams then did enough to put off Ibou Touray, as the wing-back looked to attack Richie Towell’s fine delivery.
And when Brandon Thomas-Asante escaped down the right, he sent in a low angled drive that was brilliantly tipped to safety by MacGillivray.
There was not too much happening at the other end, although the lively Williams looked dangerous when he got on the ball.
Pompey did start to enjoy more possession as the half progressed, but Vaclav Hladky was not being troubled between the Salford sticks.
MacGillivray, meanwhile, was called into action again on 26 minutes after Wilson had turned Touray’s centre towards the target.
And the keeper made an even better stop after Jordan Turnbull had spun sharply and sent in a thunderous strike.
Hladky was finally called into action moments later, although Williams’ deflected attempt seemed like it would have flashed past the post.
The Ammies were still looking more likely to break the deadlock, however, and a sliding Ash Hunter was inches away from connecting when Wilson stole possession and sent the ball across the face of goal.
Half Time: Pompey 0 Salford 0
Jackett, unsurprisingly, decided to make changes at the break and took advantage of the extra substitutions now available by making a triple switch.
Hiwula, Harvey White and Charlie Daniels all made way, as Ronan Curtis, Marcus Harness and Lee Brown were brought on, with a shift to a 4-2-3-1 system.
And Curtis made an instant impact, racing onto a long Jack Whatmough pass and forcing a stop from Hladky just seconds after the restart.
Pompey were certainly playing with a lot more confidence, although John Marquis dragged his shot past the post.
Salford were still providing threats of their own, however, with Wilson causing some problems in the Blues back-line.
But there was certainly pressure being applied by the men from Hampshire and it was just that crucial final ball that was lacking.
They went so close to falling behind on 67 minutes, though, with MacGillivray coming to the rescue once again.
He somehow denied Ash Eastham from point-blank range after the Salford skipper had met Touray’s free-kick.
MacGillivray then kept out a 20-yard attempt from Wilson and leapt on the loose ball before Thomas-Asante could capitalise.
Another substitution followed from Jackett on 73 minutes, with Ben Close given a chance to impress in place of Byers.
And his cross soon found Curtis in acres of space inside the area, only for the forward to get his acrobatic scissor kick wrong and watch the ball fly wide.
Pompey were searching for a late winner and when James Bolton’s scuffed effort was partially cleared, Harness sent the ball back into the box.
It found Brown in space and he tried to place a shot into the bottom corner, but the ball rolled narrowly past the post.
Both sides came close to finding a goal before the final whistle, with MacGillivray keeping out Bruno Andrade’s far-post header.
The Blues went straight up the other end and a stretching Marquis was not able to connect with Curtis’ cross.
But neither side could make that breakthrough inside 90 minutes and so the tie went into extra-time.
After 90 Minutes: Pompey 0 Salford 0
Pompey had a chance soon after the restart when Close cut the ball back for Curtis, but his shot was blocked before it could reach the target.
And they had a better chance just before the interval when Curtis lifted a pass into the area and Salford failed to get it clear.
It fell for Williams and his fierce strike was parried by Hladky, with an almighty scramble following before the keeper finally dived on the loose ball.
Marquis was then found in the area by Curtis, but Tom Clarke did enough to force the striker to fire wide.
Half Time: Pompey 0 Salford 0
Jackett made a fifth change during the brief extra-time interval, with Michael Jacobs on for Marquis and Curtis moving up front.
Salford were next to threaten and when their opponents could only partially clear, Jason Lowe dragged a shot wide.
Tom Naylor had a chance at the other end, but he could not force the ball through a sea of bodies after Jacobs’ corner had been nodded back by Whatmough.
Pompey were doing their best to avoid a shoot-out, but both Curtis and Close could not get shots through the defence to test Hladky.
And when Williams sent a low delivery across the face of goal, none of his team-mates could get that vital touch.
After Extra Time: Pompey 0 Salford 0
Pompey got off to a terrible start in the shoot-out, with Williams sending his effort over the bar and Curtis being denied by Hladky.
And although Brown and Sean Raggett both emphatically found the target, it ultimately counted for nothing.
Salford scored all four of their penalties – taken by Luke Burgess, Mani Dieseruvwe, Thomas-Asante and Lowe – to ensure they would lift the Papa John’s Trophy for the first time.
Pompey (4-4-2): MacGillivray; Bolton, Whatmough, Raggett, Daniels (Brown 46); Williams, Naylor (c), Byers (Close 73), White (Curtis 46); Marquis (Jacobs 106), Hiwula (Harness 46)
Booked: Bolton, Naylor, Brown
Subs not used: Ward, Nicolaisen
Salford (3-4-3): Hladky; Clarke (Loughlan 115), Eastham (c), Turnbull; Lowe, Towell (Dieseruvwe 99), Threlkeld, Touray; Thomas-Asante, Wilson (Burgess 87), Hunter (Andrade 74)
Booked: Towell, Lowe, Touray
Subs not used: Evans, Fielding, Hawkins
Referee: Carl Boyeson