Pompey will play Aldershot on July 10th in a pre-season friendly behind closed doors with a side completely made up of trialists.
There is a chance that the Shots may well go bust before then as they have to raise £50,000 by Friday to stay in business but should the friendly go ahead, Pompey's staff will run the rule over players hoping to win a contract with the club.
At least 15 trialists are expected to turn out for that match.
Gosport Borough goalkeeper Nathan Ashmore is one of them along with former France U-21 duo Malaury Martin (ex-Middlesbrough midfielder) and Herold Goulon (ex-Le Mans, Blackburn and Doncaster midfielder.)
Striker Adam Phillip will also take part in the game. The 22-year-old ex-Chelsea apprentice has just three professional appearances for Yeovil to his name.
Michael Bryan and Ryan Bird have already linked up with Pompey for pre-season and should feature against Havant & Waterlooville on Tuesday. The former is an ex-Watford winger who finished last season at Corby Town and the latter is a striker who last featured for Burnham of the Southern League.
Other trialists are Kevin Amankwaah, a 31-year-old right back who spent last season at Exeter and has also played for most of the other westcountry clubs.
Charlie Oatway Jr. is the 17-year-old son of the former Havant & Waterlooville player of the same name. He was released by Brighton this summer.
In addition to these are Hayes & Yeading forward Danny Wishart, ex-Spurs apprentice Hayes Thomas and ex-QPR defender Jake Downs amongst others.
It should be made clear that this friendly isn't just happening for Pompey's benefit. Those players that Whittingham may not want could be snapped up by Aldershot themselves or by Alex Pike of Gosport and Lee Bradbury who now manages Havant & Waterlooville.
With Whittingham's wage budget near capacity, it is going to take a very impressive performance from these players to win a contract with Portsmouth. Especially as Ricardo Rocha, Sam Sodje, Liam Walker and Shaun Cooper are still in the frame for a Pompey return.