A Fratton Park defeat accompanied by elimination from the Johnstone’s Paint Trophy.
For those connected with the Pompey Academy, however, it was a night to stand proud.
At one stage against Northampton on Tuesday evening, half of the Blues’ outfield players were the product of the club’s youth set-up.
Dan Butler, 20, and substitute Adam Webster, 19, were among a back four captained by the experienced Johnny Ertl.
Occupying two of the central midfield spots were Nick Awford, 19, and Ben Close, 18, marking their full debuts at Fratton Park.
Meanwhile, top-scorer Jed Wallace, 20, was performing wide on the right-hand side.
All drew praise from Awford, who oversaw the five while Academy chief before his own elevation into the Pompey first-team.
The hosts may have lost 2-1, yet the Blues boss was delighted with how a side with an average age around 23 fared.
He said: ‘The Academy manager (Mark Kelly) must have sat there on Tuesday night thinking what a really good scouting and recruitment system there is.
‘There were five lads who have come through your Academy all doing well, all doing their jobs, all with different qualities, all who make mistakes but all did really well. It was brilliant, absolutely brilliant for those young lads and I cannot speak highly enough of the Academy staff.
‘When I took over the Academy I didn’t realise the amount of hours involved in it put in by everybody.
‘I thank the supporters as well because it would have been easy for them to get a bit irate when we were 2-1 down and there was a little bit of a dicky spell in the second half when they pushed us back. But they didn’t.
‘It was great for Nick and Ben to start the game and you can only find out if you play them.
‘Unless you give an opportunity you don’t (find out).
‘There is this coaching model in youth football called the four-corner model where they assess physically, psychologically, technically and socially.
‘I think there should be a fifth area – opportunity.
‘If player A gets an opportunity and player B doesn’t then how can you judge them? Opportunity is massive.
‘You have got to earn the right. There is no good just thinking because you are in our Academy you have got the chance to play.
‘You have got to earn it and a lot of hard graft goes into it. You have got to be in there on merit.
‘And those five kids are really knocking on the door.’
Jack Whatmough, 18, missed out last night due to a hamstring injury.
Meanwhile, among the substitutes was 18-year-old Bradley Tarbuck, who Awford had been eager to introduce only for injuries to dictate otherwise.
He added: ‘I wanted to get Brad on but the injuries went against us.
‘I would loved to have dipped him in but he will have to wait now and take his chance when we do it – but he will get his opportunity as well.’