And as the 2020-21 season nears a conclusion, with Pompey still in the promotion mix, the Fratton faithful are already looking for signs of what they can expect from the upcoming summer transfer window – irrespective of which division the Blues might be in next term.
The News understands the current Pompey head coach will remain at PO4 beyond this season.
There’s less certainty around the 10 first-team players who will find themselves out of contract come the final game of the campaign.
So it’s fair to assume the current squad will be the focus of an overhaul regardless of the success or failure of the current promotion bid.
It’s also safe to suggest that the slate will be wiped clean in terms of previous targets identified and scouting reports filed.
After all, for Cowley to thrive in the Fratton Park hot seat and Pompey to progress under this leadership, would-be signings will have to be players whom he believes will fit perfectly with his footballing philosophy.
There’s no point in papering over the cracks or shoehorning something into place in order to make it work. It simply doesn’t work in the long term.
And with Cowley already proving he can take footballers and mould them into talents who can climb the footballing pyramid, why would you want to adopt that approach?
Take Alex Woodyard, for example, the former Concord Rangers midfielder who is now at AFC Wimbledon.
He played for Danny and his brother Nicky during their stays at Thames Road and Braintree, and accompanied them to Lincoln City, anchoring the midfield throughout the Imps’ historic 2016-17 FA Cup run – the first non-league side in 103 years to reach the quarter-finals of the competition.
Woodyard was branded as a ‘natural leader’ by Steve Evans when he signed for Peterborough in 2018, and has held his own at multiple League One clubs ever since, despite his humble footballing beginnings.
Harry Anderson is another player who Cowley took under his wing to nurture into a stand-out Football League performer.
The then Peterborough teenager first linked up with the Cowleys at Braintree, arriving on loan, before being reunited with the brothers at Lincoln in 2016.
He then signed permanently for the Imps upon their promotion to League Two, with the tricky winger not looking back since.
Now 24, Anderson is an established part of the Imps furniture, boasting 164 league appearances and racking up 24 goals and 18 assists.
Spotting and developing players Woodyard and Anderson is a tactic Cowley clearly enjoys – and one he might have to deploy again at Pompey.
Given the current financial environment in football, and the recent strain on the Blues’ finances, a track record in signing youngsters with the right attitude, talent and potential could prove beneficial.
But it’s just not at the lower reaches of the footballing pyramid where Cowley thrives in this department.
Arsenal youngster Emile Smith-Rowe is proof of that.
The attacking-midfielder is currently starring for Arsenal in the Premier League, after emerging from their youth ranks.
But before this season, the 20-year-old had barely featured for the Gunners, while only three substitute appearances came during a loan spell at RB Leipzig.
Indeed, it was not until his loan switch to Cowley’s Huddersfield in January 2020 that those outside of the Emirates began to appreciate more his undoubted talent.
When at the John Smith’s Stadium, Smith-Rowe took his opportunity with both hands, making huge strides as a player despite the Terriers being embroiled in a Championship relegation-battle.
He shined in key moments, scoring for Huddersfield in a 2-1 win against West Brom, which ultimately kept the Yorkshire side up.
So many young players struggle when they make the move from their Premier League academy comfort zones to the nitty-gritty of the EFL.
Smith-Rowe didn’t, though, and credit to Cowley for putting faith in a youngster when the pressure was on – a skill which Pompey sorely need.
Hidden gems – on loan or permanent deals – also need to be found for the Blues to stay ahead of the competition.
Managers can often be short-sighted and forget about players who once proved their talent elsewhere.
Talking of which, current League One star Jorge Grant was largely forgotten about at one point.
The prolific playmaker signed for Lincoln City in 2019, for an undisclosed fee from Nottingham Forest, just before the Cowleys left Sincil Bank for Huddersfield.
Grant showed some promise for Notts County on loan – 15 goals and six assists from midfield in 2017-2018 – but barely featured in the higher leagues or for Forest.
Yet since arriving at the Imps, the 26-year-old has been a revelation.
His 15 goals and 10 assists in all competitions this campaign is a testament to the quality that was previously undervalued.
And even though Grant has developed largely under ex-Blues boss Michael Appleton, it was Cowley who brought him in.
Left-back Harry Toffolo was another player who was cast aside by a higher echelon football club.
The 25-year-old was released by Millwall, after previously bouncing between Swindon Town and Scunthorpe United in the lower leagues.
After being discarded by a Championship outfit, Toffolo became integral to the Imps’ League Two title win, recording three goals and assists in 46 matches.
Cowley was later reunited with the defender at Championship Huddersfield in 2020.
After being deemed incapable of playing at that level two years previous, Toffolo is now a thriving first-team regular with the Terriers.
This history of spotting lost footballers, and developing youngsters into first-team regulars, is exactly what Pompey need to employ under Cowley.
Hopefully, he and his brother Nicky will write more successful transfer stories for the Blues in the upcoming seasons.