Portman Road plays host to two sides who are striving to win promotion to the Championship on Saturday.
Ipswich currently sit second in the League One standings, with Pompey two points behind in seventh spot.
But it is Emirates FA Cup first round progress that is the prize up for grabs in East Anglia on this occasion.
The Blues reached the fifth round of last season’s competition, seeing off Harrogate, Altrincham, Fleetwood and Barnsley before bowing out against eventual cup winners Arsenal.
Paul Lambert’s men fell at the second hurdle with a replay defeat to Coventry following a success over Lincoln.
Pompey have come out on top on the previous three occasions that the sides have clashed in the FA Cup.
That included a 1-0 triumph – courtesy of David Nugent’s goal – that started the triumphant run to Wembley back in 2008.
There are no replays in the competition this season, with drawn ties decided by extra-time and, if required, penalties.
Winners in the first round will receive £16,972 from The FA’s prize fund, with losing clubs awarded £5,657.
Lee Brown is set to be sidelined for around three weeks after injuring his hamstring in warm-up at Lincoln.
Pompey are also still missing Michael Jacobs (knee) and Jack Whatmough (hamstring), but Tom Naylor should be fine after going off with cramp at Sincil Bank.
Ipswich midfielder Andre Dozzell starts a three-match ban after an appeal against his red card at Sunderland on Tuesday was rejected.
Defender Luke Woolfenden is currently self-isolating, but Oli Hawkins could feature against his former club.
The hosts will also be without Flynn Downes (knee), Aaron Drinan (thigh), James Norwood (hamstring), Cole Skuse (knee) and Kane Vincent-Young (Achillles).
HEAD TO HEAD
Pompey: 13 wins
Ipswich: 19 wins
At Portman Road
Pompey: 8 wins
Ipswich: 9 wins
Referee: Andy Haines
Assistants: Anthony Da Costa and Abbas Khan
Fourth Official: Tom Bishop
Supporters in the UK can watch the contest on the BBC iPlayer, website and app, as well as BT Sport’s digital platforms.
If you are based overseas then please check local listings to see if the game is being shown in your region.
ALSO IN EMIRATES FA CUP
Games kick-off at 3pm unless stated
Harrogate v Skelmersdale (7.45pm)
Tonbridge v Bradford (12.30pm)
Exeter v AFC Fylde (1pm)
Banbury v Canvey Island
Barrow P-P AFC Wimbledon
Bolton v Crewe
Boreham Wood v Southend
Brackley v Bishop’s Stortford
Bromley v Yeovil
Cambridge v Shrewsbury
Charlton v Plymouth
Cheltenham v South Shields
Colchester v Marine
Dagenham & Redbridge v Grimsby
Gillingham v Woking
Hull v Fleetwood
Leyton Orien v Newport
Lincoln v Forest Green
Oxford United v Peterborough
Port Vale v King’s Lynn
Rochdale v Stockport
Salford v Hartlepool
Stevenage v Concord Rangers
Sunderland v Mansfield
Swindon v Darlington
Tranmere v Accrington
Walsall v Bristol Rovers
FC United of Manchester v Doncaster (5.30pm)
Scunthorpe v Solihull (12pm)
Barnet v Burton (12.45pm)
Eastleigh v MK Dons (12.45pm)
Hampton & Richmond v Oldham (12.45pm)
Havant & Waterlooville v Cray Valley (12.45pm)
Hayes & Yeading v Carlisle (12.45pm)
Maldon & Tiptree v Morecambe (12.45pm)
Torquay v Crawley (12.45pm)
Wigan v Chorley (12.45pm)
Eastbourne v Blackpool (2.30pm)
Oxford City v Northampton (7.45pm)
LAST EMIRATES FA CUP MEETING