Pompey Academy suffered stoppage-time heartache as they lost 3-2 to Liverpool in the third round of the FA Youth Cup.
Goals from Bobby Duncan and Abdi Sharif meant that Mark Kelly’s side were behind at the break in St Helens.
But they fought back brilliantly, with the lively Bradley Lethbridge netting from the spot before Joe Hancott equalised.
It looked like an extra 30 minutes would be needed to separate the teams, only for Duncan to score again with just seconds remaining.
Pompey had seen off Bristol Rovers and Cray Wanderers to reach this stage of the competition, but it was always going to be a tougher test against the Merseyside outfit.
Not that they looked over-awed against their Category One hosts, looking to get at their defence whenever possible.
Liverpool skipper Paul Glatzel did have the ball in the back of the net in the opening stages, only to have his celebrations cut short by an offside flag.
But the Blues then thought they should have been awarded a penalty for a nudge on Lethbridge by Tom Clayton.
The chances kept coming at both ends of the pitch, with Duncan drilling just past the post before a dangerous Lethbridge delivery was intercepted.
A cross from Sharif was nodded against the bar by Glatzel, but again the visitors hit back and James Whiting’s effort was saved by Vitezslav Jaros.
But it was the Reds that took the lead on 15 minutes when Haji Mnoga failed to deal with Leighton Clarkson’s corner, allowing Duncan to race through and score.
Pompey did not let their heads drop, however, and Lethbridge fired narrowly wide, before seeing another attempt well saved by Jaros.
Liverpool then doubled their advantage, as Sharif collected a fine pass from Duncan before guiding a low shot into the bottom corner.
Half Time: Liverpool 2 Pompey 0
The Blues had a mountain to climb, but that certainly did not stop them from looking to attack their hosts.
They still had threats to deal with, such as a fierce angled drive from Elijah Dixon-Bonner that was well saved by Leon Pitman.
But Pompey were given a route back into the game just past the hour mark, when Lethbridge’s free-kick was handled in the box by Duncan.
It was LETHBRIDGE who stepped up take the spot-kick and the striker confidently slammed the ball into the roof of the net.
The same player almost drew the Blues level when he met Freddie Read’s free-kick, but Jaros stuck out a hand to divert his header over the bar.
They did not have to wait long for an equaliser, however, as their opponents failed to deal with a corner and when the ball was sent back in, Lethbridge hooked it across for an unmarked HANCOTT to slot into the net.
It was Pompey looking more likely to snatch a winner as extra-time approached, with Oscar Johnston and Stan Bridgman both sending shots narrowly off target.
But there was drama at the death when Glatzel collected a short corner and squared for Duncan to slot home the winner for Liverpool.
Liverpool (4-1-3-2): Jaros; Walls, Williams, Clayton, Boyes (Savage 84); Clarkson; Dixon-Bonner (Bearne 79), Cain, Sharif; Duncan, Glatzel (c)
Goals: Duncan 15, 90+2, Sharif 33
Booked: Boyes, Walls, Duncan
Subs not used: Kelly, Brookwell, O’Rourke
Pompey (4-3-3): Pitman; Kavangah (Bridgman 63), Mnoga, Hancott, Flint; Whiting (Kelly 84), Robb, Read (c); Maloney, Lethbridge, Johnston
Goals: Lethbridge 65 (pen), Hancott 71
Subs not used: Bruce, Teggart, Stanley