Guy Whittingham has revealed there have been ‘positive talks’ over David Connolly remaining at Fratton Park.
Meanwhile, The News understands goalkeeper John Sullivan will today undergo a Pompey medical ahead of a permanent move.
The Blues are eager to add Connolly to their ranks following his impressive goal-scoring performances since January.
Whittingham has also offered the 35-year-old the chance to do coaching work at the club in addition to his playing role.
It is an aspect Connolly is keen on, having coached Spurs’ age groups when he was without a club for the first half of the campaign.
However, it is believed he is not being considered as Whittingham’s assistant – a role still to be filled. The latest round of talks with the former Republic of Ireland international took place at Fratton Park on Tuesday afternoon.
And Whittingham claims Connolly is mulling over the latest attempt to persuade him to be part of his rebuilding plans.
He said: ‘We’ve had more positive talks with David but we are not there yet.
‘He’s a good player, I want him here. He knows we have got an interest in making that happen and we are trying to work towards that.
‘Obviously, we have a budget we have to stick to and that comes into any player discussions.
‘However, I must stress, it is not only about finances with David.
‘We are looking at the possibility of another role at the club – coaching.
‘Not as a first-team coach, more other bits and pieces, such as helping the kids.
‘What he gives on the pitch is everything and you want that sort of person around both as a coach and a player.
‘He has gone away to think about that so we will see what happens, but I am encouraged.’
Definitely coming to Fratton Park will be Sullivan, following his release from Charlton.
The 6ft 1in keeper is scheduled to undergo a medical today ahead of signing a minimum two-year deal.
He will then fight it out with Phil Smith for a regular first-team spot as the Blues seek to replace Blackburn-bound Simon Eastwood.
Eastwood rejected a Pompey contract to make the switch to Rovers – a move which is expected to be confirmed next week.
In the meantime, Whittingham turned his attention to Sullivan, who was at Fratton Park for talks on Tuesday afternoon.
The 25-year-old spent the last few months of the season on loan at AFC Wimbledon, making 11 appearances.
He has been at Charlton since originally arriving on loan in March 2011, playing 12 times.
Sullivan started his career at Brighton – making 17 appearances – and has also spent time on loan at Yeovil and Colchester.