Pompey Academy have been drawn away to Gillingham in the first round of the FA Youth Cup.
The tie – which will take place at Priestfield Stadium – has to be played by Saturday, November 4.
Lead professional development phase coach Mikey Harris said: “It would have been nice to be at Fratton Park, but it’s a game that I’m sure the boys will all be looking forward to.
“It’s a chance for us to compete on a Football League surface and we saw how good the pitch was for the recent first team match.
"Hopefully we will be the ones to come out on top this time and I’m sure it will be a great experience for our lads."
“We were beaten by Gillingham in the Youth Alliance Cup earlier in the season, so know they’re a tough side.
“But hopefully we will be the ones to come out on top this time and I’m sure it will be a great experience for our lads.”
Pompey reached the third round of last season’s competition, seeing off Eastleigh and Metropolitan Police before losing to Newcastle at Fratton Park.
|FA Youth Cup first round draw|
|Tranmere Rovers v Blackburn Rovers|
|Morecambe v Wigan Athletic|
|Carlisle United v Nelson or Prescot Cables|
|Bradford City v Blackpool|
|Oldham Athletic v Bury|
|Accrington Stanley v Rochdale|
|Hartlepool United v Altrincham or Chester|
|Guiseley v Fleetwood Town|
|Gateshead or Wrexham v Salford City|
|Evesham United v Shrewsbury Town|
|Rotherham United v Bottesford Town|
|Doncaster Rovers v Walsall|
|Dunkirk or AFC Rushden & Diamonds v Tamworth or Alfreton Town|
|Stourbridge v Port Vale|
|Grimsby Town v Mansfield Town|
|Long Eaton United v Scunthorpe United|
|Chesterfield v Notts County|
|Lincoln City v Coventry City|
|Handsworth Parramore v Crewe Alexandra|
|Barnet v Wingate & Finchley|
|Colchester United v Cheshunt|
|Milton Keynes Dons v Southend Unuted|
|Leyton Orient or AFC Hornchurch v Biggleswade Town|
|Peterborough United v Cambridge United|
|Hitchin Town v Dagenham & Redbridge|
|Buckingham Athletic v Northampton Town|
|Clanfield 85 v Cambridge City|
|Luton Town v Stevenage|
|Bishop's Stortford v Boreham Wood|
|Charlton Athletic v Whitehawk|
|Bromley v Chipstead|
|Marlow v AFC Wimbledon|
|Welling United v Margate|
|Gillingham v POMPEY|
|Lewes v Camberley Town|
|Bristol Rovers v Forest Green Rovers|
|Swindon Town v Newport County|
|AFC Totton United or Ash United v Cheltenham Town|
|Plymouth Argyle v Eastleigh|
|Sholing v Clevedon Town|
|Gloucester City v Oxford United|
|Yeovil Town v Exeter City|