Pompey Academy will face Woking on November 13 as they seek to progress in the FA Youth Cup.
Andy Awford’s youngsters booked their place in the second round of the competition following victory over Southend last Friday.
Bradley Tarbuck and Liam Triggs netted in the 2-1 success at Fratton Park in front of around 700 supporters.
Now they will face Woking, who defeated Carshalton Athletic 3-1 on Monday night.
The Cards play in Football Conference Youth Alliance division B.
And Academy boss Awford, along with assistant Paul Hardyman, were there to see Woking book a Fratton Park fixture with the Blues.
He said: ‘It was a cold and rainy night at Carshalton but Woking deserved to win.
‘They were actually 1-0 down at half-time but came back to win it 3-1.
‘Woking were organised, fitter and stronger, which probably saw them over the line.
‘I’m sure they will now relish coming to Fratton Park on November 13 and we have got to make sure we don’t leave anything to chance.
‘I will certainly be looking for a better performance from our lads after the Southend match.
‘Southend are an up-and-at-them team who are in your face and very competitive. Whenever we play them you never get much time on the ball, it’s like a derby game.
‘We won 2-1 on the night, so well done for the result but the performance was not quite at the level we have had this season.
‘At half-time we were 1-0 down and staring down a barrel but we went out and showed plenty of character and spirit to dig deep like Pompey teams do and managed to win ugly.
‘We dug out a result and that’s the positive.
‘However, I’m looking for better, for more calm and composed performances, like we produce on a Saturday morning.
‘If they want to go up the ladder they have to get used to performing on occasions.
‘Manchester United players know how to handle that pressure on different occasions, it’s what they are used to.’
Meanwhile, Awford and Hardyman were among the 17,036 who took part in last weekend’s Great South Run.
Awford clocked a time of 1:31:28, while Hardyman came in at 1:33:11.
And the former Pompey favourite couldn’t resist a dig at his Academy colleague.
He added: ‘Thanks to all those who gave me a cheer in the Great South Run.
‘It was my third time and I have to admit I had a very painful couple of days afterwards.
‘I feel for Hards, though. He had to look at the back of my head and my big backside all the way around.
‘It was around eight or nine miles when the gap increased. My injection of pace unlocked the door!’