The Pompey midfielder linked up with the injury-hit National League South outfit ahead of their 5-2 defeat against Sutton United on Saturday.
He then starred for Lee Bradbury’s men in a 4-3 triumph over Wessex League premier division Horndean at Five Heads Park last night.
Now the 18-year-old central midfielder, who graduated from the Blues’ academy last term. is set to make his Westleigh Park stay formal.
Pompey boss Kenny Jackett said: ‘A loan deal is looking on the cards for Theo.
‘The Hawks are very interested in him. He wanted to go and have a look at them and he played very well.
‘It will be a good move for Theo because there isn’t a development squad at our club.
‘He’s too old for the youth team now and it will be good for him to play football.
‘The beauty is clubs are able to get a recall with players dropping down to National League South level.
‘Also, they are able to train with us. I think it is the best of both worlds.
‘It gets players regular game-time and the confidence of being out on the football ladder.
‘As time goes on, those players want to step up – which is what their aim is and ours – towards the first team.’
Widdrington played alongside fellow first-year professional Jez Beford for the Hawks against Sutton.
He then made an explosive impact against Horndean, making one and scoring anothere before half-time.
His raking cross-field pass led to Jason Prior’s opener on 20 minutes before he crashed home a 25-yard effort on 38 minutes.
After the game, Hawks boss Bradbury revealed he was keen to sign Widdrington – son of former Southampton, Grimsby and Port Vale midfielder Tommy Widdrington.