Alex Grant has joined the Hawks on loan.
The defender becomes the latest Pompey player to venture to Westleigh Park, having come back from a similar spell at Eastleigh.
Grant made just one appearance for the Spitfires – a return which disappointed Whittingham.
Now the 19-year-old has linked up with Lee Bradbury for an initial month in the Blue Square Bet South.
He follows in the footsteps of fellow Academy graduate Dan Butler, who made such an impressive impact with the Hawks recently.
Grant is earmarked to play that same left-back role, with Bradbury eager to find a replacement for Butler.
The youngster can also play in the centre of defence – a position he occupied in the Capital One Cup against Plymouth this season.
And Whittingham is hoping Grant’s latest loan spell will at last offer him regular football.
He said: ‘It didn’t work out for Alex at Eastleigh.
‘At Havant they want him to go and play, so that’s the reason for him to go there.
‘Dan Butler went there and improved over a few months, so hopefully Alex will go and do the same, get games under his belt and become a better player.
‘We know we can trust Lee (Bradbury) and Shaun Gale to look after him and who knows, six weeks down the line after regular football he could be called into our first team.
‘The thing with Alex is he can play left-back as well as centre-half and quite possibly may take up the role Dan had while he was there.
‘A lot of players have that versatility.
‘The way football is going in the lower leagues and the size of the squads you are going to need that.
‘I’m hoping he can get the games he needs to help with his development.’
Grant made his Pompey debut alongside Butler and Jed Wallace back in August in the Capital One Cup match at Home Park.
Yet weeks later he damaged knee ligaments in training and was forced on to the sidelines.
As a result, his colleagues set off for non-league spells while he was making his injury recovery.
Last month he joined Eastleigh but selection and the weather restricted him to one match.
Meanwhile, loanee Frankie Sutherland has been called up to the Republic of Ireland under-21s for the first time.