As Pompey miss two of their regular centre-backs, Adam Webster and Adam Barton are the men expected to face a stern test as Ipswich boast four quality strikers to choose from.
Steve Wilson runs the rule over the Tractor Boys’ attacking options for tomorrow’s Cup clash.
Born in Waterford, Ireland, Daryl Murphy initially started his career at Luton Town but was released in 2002, before signing for his hometown club.
But the Irish connection worked in his favour when Mick McCarthy left his role as boss of the national team and took him to Sunderland in 2005.
Another Irishman, Roy Keane, eventually replaced McCarthy and took the front man with him to Ipswich for his first spell of a lengthy association with the club in 2010.
Celtic then came calling later that summer, but he returned to Ipswich on a season-long loan in 2012, before moving permanently in 2013.
Although he is not a prolific goalscorer, Murphy is capable of bursts – as he proved in November with six goals in four games, which earned him the Championship player-of-the-month award.
A hat-trick against Rotherham (November 7) ended his goalless start to the campaign, and at the time McCarthy offered some unique praise.
‘I said “welcome back Murph, we don’t want to see your sister again who’s been playing in recent weeks”. You can get away with it when he’s scored a hat-trick,’ explained McCarthy.
At 6ft 3in, Murphy’s a handful in the air and a physical threat. The 32-year-old has scored seven goals in 27 appearances this season and has been capped 16 times by Republic of Ireland.
In recent weeks, Mick McCarthy has opted to partner Freddie Sears alongside Daryl Murphy in attack.
The 26-year-old burst on to the scene with West Ham in 2008 when he scored five minutes into his debut.
But he then failed to nail down a regular place under Gianfranco Zola and was sent out on loan to Crystal Palace.
Sears failed to score for the Selhurst Park outfit and more loan spells followed at Coventry, Scunthorpe and Colchester as he was deemed surplus to requirements under Sam Allardyce at Upton Park.
His loan stay at Colchester started in February 2012 and that became a permanent move later that summer.
After scoring 14 goals for Colchester last season, including two in the FA Cup first-round clash with Gosport Borough at Privett Park, Sears signed for Ipswich for £100,000 last January when his contract was set to expire in the summer.
And he continued that goalscoring form at Portman Road, netting nine goals in the second half of last season.
Seen as a natural finisher and a clever predator in and around the penalty area, Sears has six goals to his name from 25 appearances this term.
The Jersey-born striker has a fine goalscoring record down the years.
He started his career with Bournemouth after emerging from the youth ranks with a prolific record and went on to play aivotal role as the Cherries made their way up the divisions in recent seasons.
After 59 goals in 173 games, the 27-year-old moved on to Bristol City in 2010, where he scored 20 goals in 77 outings.
A loan return to Bournemouth followed in December 2012 and he made the permanent switch back to his old stomping ground in January 2013.
Pitman then made 39 appearances and scored 14 goals as Bournemouth claimed the Championship title last term.
But with his first-team opportunities often restricted to being a substitute, the front man opted to stay in the Championship and made the move to Ipswich for an undisclosed fee.
Since then Pitman has found it difficult to find a regular starting berth but has still netted seven goals in 26 games.
He’s unorthodox but well capable of producing something out of the ordinary. And although not lightning quick, he has real ability and ill shoot from anywhere.
Former Pompey forward Luke Varney may be in line to make his first start for Ipswich against his old club.
The 33-year-old spent a short spell at Fratton Park back in 2011-12 at a time when the Blues appeared to be just starting to get back on their feet again.
He was a summer recruit ahead of Steve Cotterill’s second season for a fee believed to be in the region of £750,000, with club owners CSI giving their financial backing to the manager.
Varney made a goalscoring start to his Pompey career, netting a late equaliser in a 2-2 draw at Middlesbrough, and went on to make 31 appearances – scoring six goals.
His best game came in a 3-1 win over Doncaster under the caretaker management of Guy Whittingham, although he was also in the side that grabbed a famous 2-2 draw at Southampton after the financial troubles resurfaced.
Varney was one of the many players to accept a pay-off from a lucrative contract after Pompey were relegated and he moved on to Leeds in July 2012.
But he moved to Blackburn two seasons later and joined Ipswich on a permanent deal in December to provide cover for the loss of David McGoldrick, who is out with a long-term hamstring injury.
Sharp and quick, Varney can play through the middle or out wide but has been used as a substitute in his four appearances so far and has yet to score this season.