On paper, it’s by far Pompey’s toughest test to date.
The Blues travel to Premier League-chasing Norwich in the third round of the FA Cup on Saturday.
The Canaries are flying high in the Championship this campaign, sitting in second spot behind Leeds.
Although Kenny Jackett’s side top League One, they’re in for a stern examination at Carrow Road – even despite home boss Daniel Farke likely to make wholesale changes.
For as strong as Pompey’s current squad is, there aren’t many with second-tier experience under their belt.
In fact, only seven of Jackett’s troops have featured in the division above.
Brett Pitman has spent a significant part of his career in the Championship, representing AFC Bournemouth, Bristol City and Ipswich.
The Blues skipper netted 13 goals when the Cherries were promoted into the top flight during the 2014-15 season.
Tom Naylor was plying his at the level above for the past two seasons before moving to Fratton Park from Burton Albion in the summer.
The midfielder has 68 appearances in the Championship during his career.
Matt Clarke will undoubtedly continue his trajectory up the Football League ladder. There’s arguably not a better defender than him in League One.
The centre-back was brought to Pompey by Paul Cook in 2015. He’d played four times for Ipswich during 2014-15 in the second tier as a teenager.
Christian Burgess arrived the same summer as Clarke. The defender made a solitary outing for Middlesbrough on the final day of the 2013-14 season.
Ben Thompson is set to play his final game for Pompey before returning to Millwall.
The midfielder has endeared himself to the Fratton faithful following a highly-impressive loan spell.
But despite him being recalled, Thompson made only three substitute appearances for the Lions last term.
Andre Green and David Wheeler are also on loan at Pompey from Championship outfits Aston Villa and QPR respectively.
The former played twice for Villa in the Championship this term before moving to the Blues in August, as well 18 times in total beforehand.
Wheeler represented QPR on nine occasions during 2017-18.