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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21. Aiden O'Brien (ST) - Sunderland
O'Brien became Pompey's fifth and final winter signing as details emerged quickly on deadline day. Much like Webber, has signed a short-term deal until the end of the season. Picture Lewis Storey/Getty Images Photo: Lewis Storey
22. Jamie Lindsay (CM) - Rotherham
After Pompey found themselves light in midfield, they moved for Jamie Lindsay. However, they saw their opening offer rebuffed by Rotherham before the deal fell flat. Could be one to keep an eye on in the summer. Picture: Nathan Stirk/Getty Images Photo: Nathan Stirk
23. Lewis Wing (Winger) - Middlesbrough
Pompey pushed hard to bring Wing to Fratton Park, but a deal collapsed due to the complicities of the transfer. However, tempers flared across the Fratton faithful when Wycombe were able to sign him hours later. Picture: Jacques Feeney/Getty Images Photo: Jacques Feeney