Dave Watson’s side travel to Fratton Park looking to improve on their showing in last year’s competition, when they were eliminated by AFC Wimbledon in the last 32.
Members of the EFL Youth Alliance, Pompey have already had to see off two sides to set up this evening’s clash – overcoming Eastleigh and Metropolitan Police to secure their place in the Third Round.
United, meanwhile, ended a torrid run of league form with a comeback win at Wolverhampton Wanderers last week – a result Bailey felt was “crucial” ahead of their trip to the South Coast.
The 17-year-old feels the mood in the Magpies’ camp has been lifted on the back of their victory in the Black Country, but – with last season’s premature Youth Cup exit still fresh in the mind – insists that he and his teammates will not be getting ahead of themselves anytime soon.
“I think everyone’s a little bit more excited than normal, but we’re just trying to prepare for it the same as any other game – we don’t want to overhype it in case we end up doing what we did last year where we got beat surprisingly,” he told nufc.co.uk.
“We’ll be taking it a game at a time, and we just want to do as well as we can and stay in the competition. First of all, we just need to try and beat Portsmouth. They’re an ex-Premier League club so I’m sure they’ll have a good side, and we’ll have to be at our best.
“Coming off a poor run, I think it was crucial that we got the win last week. There’s a big game coming up and we need as much momentum as we can get, so obviously it has lifted the spirits, and everyone is positive again now.
“It showed that if we do go a goal down, we can come back – and that’s massive for the team. We’re a good unit, and we’ve shown we have character.”
As well as playing a starring role for the Magpies’ Under-18s, Bailey has also racked up a string of appearances for Peter Beardsley’s second-string this term, the latest of which came against West Bromwich Albion at Whitley Park last month.
On that occasion, he lined up alongside first-team players Massadio Haidara, Achraf Lazaar and Daryl Murphy, having been handed a starting berth ahead of the likes of Curtis Good and Lubomir Satka.
Thus far, the youngster is pleased with the progress he has made this season, and thanked his teammates for playing their part as he looks to keep balancing his commitments.
“All the lads have really helped out, and the transition has been quite good,” he said. “The older ones have made me feel welcome, and my own team haven’t tried to stitch me up or anything like that! All of the coaches have helped, too.
“Things are going well, and I just want to keep it up. Hopefully I can get back involved with the 23s, and hopefully have a good run with the 18s and get the confidence going again.”
