The former Gillingham left-back has joined the Blues on a two-year-deal, with the club having the option of a third, after turning down the offer of a new deal at Priestfield.
He represents Pompey’s ninth signing of the transfer window and Cowley is delighted to land a player who he believes has all the attributes to be a success at Fratton Park.
Welcoming 25-year-old Ogilvie to the Blues, the head coach said: ‘Connor is someone who’s been a really consistent performer at League One level for a number of years.
‘He’s won player of the season awards for Gillingham and was a key member of their side after coming through at Tottenham.
‘Being able to play as a left-back or a left-sided centre-half offers us versatility and also real competition for places, which is crucial in a 46-game season.
‘Connor has got a lovely range of passing and has got technical attributes, while he’ll weigh in with goals as well.
‘He’s got the qualities that Pompey fans will like to see – he’s brave and willing to put his head in where it hurts.
‘That physicality will be a really big asset for us and so we’re delighted to bring Connor into the club.’
Ogilvie will compete with Lee Brown for the left back berth.
A player who can also play at centre-back, he played 171 appearances for the Gills, scoring 10 goals.