The 25-year-old is available on a free transfer after turning down a new contract at Gillingham last season, a club where he has made 171 appearances and scored 10 times.
Danny Cowley is keen to add competition to the left-back position currently filled by Lee Brown.
That has brought former Spurs defender Ogilvie to the Blues’ head coach’s attention in the approach to Saturday’s League One curtain-raiser at Fleetwood.
We caught up with the Kent Messenger’s Luke Cawdell for the full lowdown on the Pompey target…
Wait a minute, didn’t Connor Ogilvie leave Gillingham?
‘Connor was offered a new contract at the end of last season, but rejected it.
‘He then went off to look for a new club in the Championship, with one rumoured to be Luton, which, at that level, is the size of club I think he’d be looking at.
‘It turned out nothing happened – then he rocked up for Gillingham’s pre-season.
‘Connor completed the full 90 minutes in last month’s friendly against Colchester and has been around ever since.
‘Basically, Gillingham’s contract offer is still on the table, despite having written him off as leaving at the end of the season.
‘Steve Evans is happy to have him back. However, Gillingham aren't going to be able to compete financially with most of the clubs, so if someone does come in with a better offer then it’s just down to whether Connor wants a new club.’
How has he done in pre-season?
‘Following Connor’s 90 minutes against Colchester, he collected a groin injury against Millwall during 45 minutes last Tuesday.
‘That meant he was an unused substitute against Leyton Orient at the weekend, so I don’t imagine the injury is too serious.
‘Steve Evans afterwards said he didn’t want to take a risk on the player. He also said in passing that Connor was still training with them with a view to possibly leaving.
‘That, of course, may now have changed.’
What sort of left-back is Ogilvie?
‘Connor arrived permanently at Gillingham on the same day Steve Evans was appointed manager in May 2019, so it’s up for discussion about who actually signed him.
‘What is under no doubt, however, is that he has played his best football under Evans, particularly at left-back.
‘He had a few loan spells here before Evans came in, but, as a left-back he didn’t pull up any trees. He played better as a left-sided centre-back.
‘At that stage you wouldn’t have thought he could be a Championship player, yet Connor has definitely improved under this manager.
‘He’s not a bombing forward type of wing-back, more defensive-minded, but what he has got is a knack of scoring winning goals. He seems to be in the right place at the right time.
‘For me, he is potentially a Championship player, probably in the lower half.’
How do Gillingham see the situation with his contract?
‘At the end of the season, everyone thought Connor had gone. It was a case of best of luck, you've done well, you’re a Championship player, well done.
‘The next thing is he’s back, so it gets everyone thinking he’s going to sign. Now it’s looking like he might not.
‘People would be happy if he does stay, while Steve Evans doesn’t bear grudges. This summer Max Ehmer has returned following an unsuccessful year at Bristol Rovers after leaving the Gills.’
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