Pompey have already progressed in one cup competition in the past couple of days and now they will look to do the same again tonight.
Having seen off Rochdale on Sunday afternoon, the Blues are back on home soil to face Arsenal U21s in the second round of the Checkatrade Trophy.
Kenny Jackett’s side reached this stage by winning three matches to secure top spot Southern Group A.
Victories over Gillingham and Crawley took them into the knockout stages with a game to spare, while beating Tottenham’s youngsters guaranteed a home tie.
Their opponents were runners-up in Southern Group E, finishing behind Cheltenham on goal difference.
It is the Gunners’ first season in the competition, having opted not to enter a side in each of the previous two campaigns.
They also compete in the top tier of Premier League 2 and are currently in sixth position after 11 games.
Pompey have not faced an Arsenal side since both were in the top-flight in 2009/10, with the Londoners winning both encounters 4-1 that term.
Jackett is expected to make multiple changes to his side, with their previous match having taken place just two days earlier.
Dion Donohue (hamstring) and David Wheeler (back/hamstring) are missing, while Joe Mason (groin) is also a doubt.
HEAD TO HEAD*
Pompey: 14 wins
Arsenal: 32 wins
At Fratton Park
Pompey: 8 wins
Arsenal: 13 wins
*Matches against Arsenal’s first team
Fans can secure their seat online here or by visiting the Anson Road ticket office.
Please note that only the Fratton End and ‘A’ Section of the South Stand Upper are open for this fixture.
Fans buying tickets this evening can visit the ticket offices in Anson Road or Frogmore Road, while there will be cash sales on the cobbles underneath the South Stand.
Ticket collections can be made from main reception from 5.30pm, while turnstiles will open at 6.30pm.
Fans are advised that the Victory Bar will not be open this evening.
Supporters in the UK and Ireland can watch the action live, with commentary and graphics. It is priced £10 for a match pass.
Please note that subscribers will still need to purchase a match pass in order to watch the game live.
Overseas subscribers and match pass holders can watch the action, with commentary starting from around 10 minutes before kick-off.
ALSO IN CHECKATRADE TROPHY
Cambridge v Northampton
Chelsea U21 v AFC Wimbledon
Cheltenham v Newport
Exeter v Peterborough
Luton v Southend (Wed)
Swansea U21 v Bristol Rovers (Wed)
Oxford v Tottenham U21 (Dec 18)
Accrington v Lincoln
Barnsley v Man City U21
Mansfield v Bury
Newcastle U21 v Macclesfield
Port Vale v Stoke U21
Sunderland v Notts County
Rochdale v Oldham (Wed)
Shrewsbury v Walsall (Wed)
LAST TIME OUT