Jayden Stockley dominates the list of those who got away – yet the collapse of Corey Addai’s proposed move is similarly exasperating.
The Blues’ head coach has been scouring the Football League and non-league scene for a third-choice keeper since before the end of last season.
With Duncan Turnbull informed he wouldn’t be handed a fresh deal and packed off to Las Vegas Lights on loan for the remainder of his Fratton Park days, Cowley has long looked elsewhere.
The criteria is simple – young, promising and with fewer than five appearances to their name.
Cannily, the latter stipulation would enable the Blues to bring in an emergency keeper should the need arise.
Nonetheless, despite the third-choice role being considerably down his recruitment list in terms of importance, it has been tough to fill.
With Gavin Bazunu and Alex Bass battling it out to be first choice, auditions for the final keeper have taken place since the return to pre-season training.
In the opening week, at least two triallists worked with new first-team goalkeeping coach Michael Poke, albeit without impressing sufficiently to earn longer stays.
Then, at the start of the second week, Addai arrived.
Measuring at 6ft 7in, aged 23 and with two career appearances – both during a National League loan spell at Chesterfield, he ticked the boxes.
Previously with Arsenal, Coventry and Barnsley, Addai spent three weeks under Cowley’s scrutiny, including the intensive training camp at St George’s Park.
The keeper’s towering presence and comfort on the ball had drawn nods of admiration from players and management alike.
His involvement at St George’s Park also grew in importance, with Bazunu’s quad injury keeping him out of some sessions.
Unlike many of the triallists, Addai’s presence was not merely a short-term marriage of convenience. Rather it represented a long-term vision.
Sure enough, following a second-half outing in place of Bass at Bristol City last week, Cowley moved to close a deal.
It would finally represent the culmination of the long-running hunt for Pompey’s third-choice keeper.
As it turned out, the potential switch collapsed.
Cowley declined to go into detail after Saturday’s 1-1 draw at Luton, yet the disappointment was obvious.
It is understood the circumstances had nothing to do with financial issues, with Pompey’s budget comfortably able to absorb his proposed wages.
Regardless of the reasons which prompted the deal to be scrapped, Cowley is back to square one.
And so the hunt for a suitable third-choice keeper begins all over again. Another position for Pompey’s boss to fill in a largely exasperating summer transfer window.
A message from the Editor, Mark Waldron
The News has launched a subscription offer which gives you unlimited access to all of our Pompey coverage, starting at less than 14p a day.
You can subscribe here to get the latest news from Fratton Park - and to support our local team of expert Pompey writers.