Pompey have been plagued with injuries across the back-line this season with captain Clark Robertson and Paul Downing facing lengthy spells on the sidelines.
This has seen the former Lincoln boss adapt to his personnel crisis by shoehorning midfielders and full-backs into a back-three.
And the Blues have suffered dearly as a consequence by conceding 11 goals in their last five league games.
However, it may not be as easy at it appears to bring new faces into the club with the January window notoriously difficult to operate in.
As a result, Cowley may have to look for a short-term fix by looking towards the free agents, or at those whose current deals are set to expire.
Click through the list to see who could arrive on the south coast on a free transfer or for a cut-price deal.
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13. Alex Baptiste: Bolton Wanderers
Another veteran on the list, Alex Baptiste has enjoyed a long career at clubs such as Blackpool, Middlesbrough and the Trotters. Despite his advancing years, the 35-year-old has made seven appearances in the league this season and scored against MK Dons in August. (Photo by Lewis Storey/Getty Images) Photo: Lewis Storey
14. Joe Walsh: Lincoln City
Joe Walsh could be available for transfer this January after playing only twice in the league this season. The 29-year-old played the entirety of Lincoln's 2-1 victory against Charlton last month but has been omitted from 14 matchday squads this term, but more recently due a quad strain sustained against AFC Wimbledon.(Photo by Joe Portlock/Getty Images) Photo: Joe Portlock
15. Ryan Inniss: Charlton Atheltic
The 26-year-old was an ever-present for the Addicks earlier in the seasons but has missed the last two months due to a thigh injury sustained in September. (Photo by Jacques Feeney/Getty Images) Photo: Jacques Feeney
16. Joseph Olowu: Doncaster Rovers
The former Arsenal starlet could be another to follow the path trodden by Emile Smith Rowe and Miguel Azeez to link up with Danny Cowley. The 21-year-old has already shown versatility this season to play at centre-back and left-back which could make him a viable option for Pompey. (Photo by Pete Norton/Getty Images) Photo: Pete Norton