Another Dan Gifford hat-trick was in vain, as Pompey exited the FA Youth Cup following an extra-time defeat to Cheltenham.
Brennan Denness-Barrett's brace had given the Robins a comfortable advantage at the home of Evesham United.
But Gifford (pictured) – who struck three times in Saturday’s league win at Forest Green – then netted twice after the break to ensure the second round tie would require an additional 30 minutes.
A fine Connor Jakeways effort and Felix Miles strike meant the Blues had to battle back again and although Gifford completed his treble, they were unable to find a leveller.
Professional development phase coach Liam Daish said: “We didn’t start the tie right and were second best all over the pitch throughout the first half, conceding two poor goals.
“You can’t dress it up – the defending wasn’t good enough. But we were more aggressive after the break and started to play on the front foot.
“Dan got a couple of goals to put us back on level terms, but then – once again – the beginning of extra-time saw us begin slowly.
“Out of all the goals scored by Cheltenham, for the third one we just had to hold our hands up and say it was a great strike.
"None of us can grumble about the result because we got back into the contest, then tossed it away again."
“He hit it sweetly from 25 yards and gave Toby Steward no chance. That was the only bit of quality they really needed and the rest were down to our mistakes.
“It was end-to-end from that point and we conceded again before Dan gave us some hope towards the end.
“But we didn’t get through those key moments as well as we could have and that meant we left ourselves with a mountain to climb and were always chasing. We were never in control.
“You can’t knock Dan because he works incredibly hard up front and took his goals well – his record doesn’t lie.
“That’s two hat-tricks in as many games and I feel for him. I’m disappointed that it didn’t get us the win.
“A real positive was that we finished the tie with four 16-year-olds on the pitch and Maxwell Hurst changed our dynamic when he came on through sheer endeavour.
“Looking back over the whole game, though, none of us can grumble about the result because we got back into the contest, then tossed it away again.”
Pompey: Steward; Setters, Kaba (c), Dockerill, Hughes; Jewitt-White, Simpson (Hurst 64); Williams (Aston 46), Payce (Bosaka 85), Bridgman (Laidlaw 111); Gifford
Subs not used: Bennett, J.Fox, Traynor