Firstly, it’s the day that will see the contracts of both Joe Morrell and Zak Swanson officially expire, with no white smoke yet to emerge from talks over possible Fratton Park extensions - 61 days after the Blues announced their retained list.
Secondly, it’s the last day before certain members of the Pompey first-team enter the final year of their current deals, giving the Pompey hierarchy plenty to think about over the next 12 months.
In total eight players will potentially be available on free transfers if new terms are not reached. In fairness, there’s plenty of time to have those chats. Meanwhile, John Mousino told The News earlier this month that Pompey will move to secure the futures of their big contracted assets this summer to avoid any issues.
But who are the eight who will be at the centre of those discussions? Here’s what we discovered.
1. Colby Bishop
The striker has bagged 45 goals in 100 appearances for the Blues since his £500,000 move from Accrington in 2022. That works out at a goal every 2.2 games, which will prove more than handy in the Championship this season. The club have the option of an extra year on a player who turns 28 in November. Photo: Bryn Lennon
2. Regan Poole
The central defender adjusted to life at Fratton Park seemlessly last season after his free transfer move to Lincoln. That brilliant start to his Pompey career was unfortunately cut short last November as the 26-year-old suffered a season-ending ACL injury against Chesterfield. He's due to return to full training next month, with Pompey no doubt keeping a close eye on Poole's progress. | Jason Brown/ProSportsImages
3. Conor Shaughnessy
One of the stars of the season last term as the Irishman's defensive qualities and eye for important last-minute goals helped steer the Blues to the League One title. The defender's stock has clearly risen since his free-transfer move from Burton last summer. His next deal won't come cheap if Pompey want to keep him. | Jason Brown/ProSportsImages
4. Jack Sparkes
Another player who proved invaluable to Pompey last season as the free-transfer signing from Exeter stood in admirably as Connor Ogilvie battled against injury. It will be interesting to see how he steps up to the rigours of Championship football this season. | National World