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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13. Josh Sims (Winger) - Free Agent
Josh Sims has been a free agent since his Southampton release in the summer, and still remains unattached in February. Pompey were linked to his services in June, but Sims remained without a club after battling health problems. Picture: Alex Pantling/Getty Images Photo: Alex Pantling
14. Tom Pearce (LB) - Wigan Athletic
Pompey's interest in Pearce significantly cooled after the signing of Denver Hume, especially with the Blues paying less for the Sunderland man when compared to what it would have to taken to sign the Wigan man. He was the other major consideration along with Hume but signed a deal with the Latics to put that talk to bed. Picture: Michael Regan Photo: Michael Regan
15. Cameron Archer (ST) - Aston Villa
Pompey joined a number of clubs in the EFL looking to sign Cameron Archer from Aston Villa. Danny Cowley is a huge admirer of the starlet but ultimately missed out on his services, with Preston winning the race for his signature . Picture: James Chance/Getty Images Photo: James Chance
16. Tariq Uwakwe (CM) - Chelsea
Despite Cowley being an admirer of Uwakwe, Pompey never moved for his services last month. As a result, the 22-year-old moved to Crewe permanently from Chelsea. Picture: Alex Pantling/Getty Images Photo: Alex Pantling