It felt like barely a day passed without a new name being linked with a switch to Fratton Park.
But how have those who didn’t arrive or moved elsewhere fared since?
Some have failed to make the kind of impact for Pompey fans to feel they’ve missed out, while others have seen their value soar.
Here’s the men who didn’t arrive at PO4 – and what they’ve done since.
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21. Shane Ferguson
A goal for club and country amid 42 outings, as the Northern Ireland winger moved to League One leaders Rotherham from Millwall. Photo: Dan Istitene
22. Owen Dale
A player Cowley was keeping tabs on but only if there decent money generated with sales. Moved to Blackpool from Crewe and has scored a single goal from 15 games. Photo: Clive Brunskill
23. Ben Thompson
Mentioned with a move to Pompey once or twice in the past... joined Gillingham from Millwall on loan and made 11 appearances as Neil Harris' side impress. Photo: Joe Pepler
24. Jordan Lawrence-Gabriel
The right-back was mentioned but unlikely Pompey had the clout to offer the former Nottingham Forest man the four-year deal he signed at Blackpool. Photo: Alistair Langham