Danny Cowley secured the services of Hayden Carter, Tyler Walker, Ollie Webber, Denver Hume, and Aiden O’Brien before the clock hit 11pm.
And seven faces also departed Fratton Park, as the Blues boss’ south coast overhaul continued.
But what happened to the other names linked with a south coast move last month?
Click through the list to see the outcomes to the names touted for a switch to Pompey this winter.
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5. Omar Rekik (CB) - Arsenal
Rekik is considered one of Arsenal's brightest stars, and Danny Cowley had watched him on a number of scouting trips. The defender looked set for a loan move to Stoke on deadline day before the move collapsed. Picture: Alex Burstow/Getty Images Photo: Alex Burstow
6. Dylan Bahamboula (CM) - Oldham Athletic
Pompey were apparently one of a host of clubs interested in the Oldham star's signature. His contract expires in the summer which allows him to leave on a free transfer at the season's end. With the Blues already well stacked in the midfield department, and if the rumour was true (we have our doubts) any move would come in the close season. Picture: James Gill/Getty Images Photo: James Gill
7. Liam Cullen (ST) - Swansea City
Swansea striker Cullen was on Pompey's list of potential targets this winter, but wasn't a priority. And this turned out to be true with the Blues seeking alternatives, while the forward joined Lincoln on loan. Picture: Steve Bardens/Getty Images Photo: Steve Bardens
8. Will Boyle (CB) - Cheltenham
Cowley had refused to comment on speculation linking the Robins captain with Pompey out of respect to his current employers. However, The News understood he was high on a list of potential targets with the Blues boss aware of his ability. But with his contract expiring in the summer, the club reprise their interest in the close season. Picture: Shaun Botterill/POOL/AFP via Getty Images Photo: SHAUN BOTTERILL