The painful memory will never leave Andy Awford – nor his former youth team colleagues.
A 10-0 defeat at Spurs, a result against an under-18s Pompey line-up featuring Awford, Darren Anderton, Kit Symons, Mark Kelly and Darryl Powell.
You may have heard of them? Fair to say that little lot bounced back from such a mauling to enjoy excellent Football League careers.
For Awford, the reaction from the current crop of Academy youngsters will dictate whether they can follow suit.
A 7-0 demolition by Southampton in the FA Youth Cup on Tuesday night was heartbreaking for the Blues players on display, many of them hailing from the local area.
The chasm between the divisions, set-ups and finances ensured it was always going to be a massive ask to get something from the match.
Regardless, Awford looks back on being at the receiving end around the same age.
And he has stressed the importance of those wounded Pompey youngsters now showing the right attitude to come back from that body blow.
He said: ‘I got beaten 10-0 as a youth team player away at Tottenham and there were some very good players in that team.
‘The likes of Anderton, Symons, Powell, Mark Kelly and all that crew and we got beat 10. I was a schoolboy, while Peter Osgood was the youth-team coach.
‘Like I said to the lads on Tuesday night, it is how you respond.
‘Not all those Southampton players will get contracts, that’s how football is.
‘We all know that and I have told that to the players, you know the ratios.
‘So where are those Southampton players going to go when they get released from there? It has a knock-on effect.
‘That result will be an eye-opener for our lads.
‘They are better than they showed but there is still a gap they need to bridge and we will continue to work with them.
‘I think we have some good players in our Academy, I really do, but might just have found one or two maybe aren’t quite as good as we thought they were.
‘They have to learn from it and if they learn from it and go on to be better players then it is worth getting beat 7-0.
‘If they don’t learn from it then there’s no point.
‘They won’t be the only team that go there and get beat 7-0, believe you me.
‘And it will happen again in their careers at different levels, that’s what football is about. Now it’s about how you respond.
‘What we are looking at is who is going to poke their head above the parapet, who is going to be the one who shines through this season.’
One player to emerge with any credit from the fixture was keeper Alex Bass.
The schoolboy has been sharing duties with Alfie Raine this season, both stepping up from the age group below.
And some marvellous saves certainly prevented a double-figure scoreline.
Awford added: ‘Alex played very well. When you have that much to do you are going to make some saves. It was a save every four or five minutes, so well done to him.
‘He kept the score down to single figures in my opinion and again it is a learning curve for him to move forward, after all he is only 16 and still at school.
‘It might just make some people realise where we are at.’