Pompey mounted an incredible comeback to beat Gosport on penalties and reach the third round of the Hampshire Cup.
A young side – made up entirely of academy players – found themselves three goals down early in the second half following strikes from Alex Barsa, Harry Medway and Rafa Ramos.
But Koby Mottoh (pictured) pulled one back for the Blues and Connor May then struck to set up a tense finale at Privett Park.
And they levelled in stoppage-time, with Mottoh scoring from the spot after Medway had been dismissed for a handball.
It meant that there would be a penalty shoot-out and with Gosport failing to net either of their first two, Mottoh struck to ensure Pompey eventually triumphed 4-3.
The Blues made a lively start on a warm and humid evening and a teasing Kevin Bosaka delivery was just out of reach for Sam Folarin.
The striker did have a chance soon after, but saw his long-range drive fly straight into the arms of Callum Smart.
It was Bastian Smith who was the busier of the two keepers, however, and he did well to deal with a deflected Antonio Diaz effort.
And the teenager made some other decent stops as the first half progressed, one of which from Ramos led to Spencer Spurway having to hack the ball from the line.
But the hosts did take the lead on 24 minutes after Smith dealt with a cross, but the ball only travelled as far as Barsa.
The midfielder did well to make space for himself on the edge of the box before drilling a shot into the bottom corner.
Pompey were struggling against their older and more physical opponents, although Folarin fired over after skipping past a couple of challenges.
And they found themselves further behind on 41 minutes, as Medway met Kurtis Cumberbatch’s cross with a header that looped after Smith and into the net.
The visitors might have found a route back into the contest just before the break, but a diving Smart managed to get a fist on Mottoh’s excellent right-sided cross.
Half Time: Gosport 2 Pompey 0
There were not even two minutes of the second half played when Gosport increased their lead further.
It was an inviting cross from Barsa that Ramos rose to meet in the box and a powerful header left Smith with no chance.
Pompey had the opportunity to pull one back when Jayden Keteku was brought down on the edge of the box, but the wall did their job to block Mitch Aston’s free-kick.
Then, following some tricky footwork from Folarin, a Keteku attempt was deflected narrowly past the post.
Gosport were still creating chances of their own, though, and a corner led to an almighty scramble in the box before the ball was eventually booted clear.
The young Blues, to their credit, kept battling away and after cutting in from the right, Mottoh’s low drive tested the handling of Smart.
And it was MOTTOH who did reduce the deficit on 69 minutes, courtesy of a neat angled finish from just inside the box.
It certainly provided an injection of confidence, with Pompey starting to pass the ball around with much more confidence.
They set up a tense finale when Folarin stole possession inside the box and unselfishly cut back for substitute MAY to slot home from a few yards out.
And there was more drama in stoppage-time when Medway used his hand to divert Mottoh’s shot against the bar.
Referee Rob Ablitt pointed to the spot and dismissed the defender, with MOTTOH coolly rolling in the penalty to take the tie to a shoot-out.
After 90 Minutes: Gosport 3 Pompey 3
Zak Sharp fired the first spot-kick over the bar and an effort from Jake Wright was then well saved by Smith.
May and Spurway both converted their penalties, but Smith’s strike rattled against the underside of the bar.
Folarin made no mistake, however, and although Cumberbatch, Jonny Efedje and Ramos all scored for Boro, Mottoh stepped up to send Pompey into round three.
Gosport (3-4-3): Smart; Sharp, Mann, Medway (c); Wright, Hookey, Cumberbatch, Efedje; Barsa (Ayre 87), Diaz (Towse 72), Ramos
Goals: Barsa 24, Medway 41, Ramos 47
Sent off: Medway
Booked: Mann, Sharp
Subs not used: Pope, Wingfield, Dougan
Pompey (3-5-2): Smith; Murray, Spurway, Fox (c) (May 57); Mottoh, Staight (Howard 82), Aston, Keteku, Bosaka; Clout, Folarin
Goals: Mottoh 69, 90+2 (pen), May 83
Booked: Spurway, Folarin
Sub not used: Glover
Referee: Rob Ablitt
Attendance: 701