Earlier this week, the Pompey boss saw three of his former loanees involved in Arsenal’s victory over Chelsea.
Emile Smith Rowe who started, and scored, in the 4-2 victory for the Gunners made 19 appearances under the current Blues head coach at Huddersfield.
Another of his Terriers contingent, Trevor Chalobah, was an unused substitute for Chelsea at Stamford Bridge, while a familiar face to the Fratton faithful, Miguel Azeez, was deemed good enough by Mikel Arteta to make the bench in west London.
For the ex-Lincoln boss, seeing players he signed on loan flourish in England’s elite competition has provided a huge source of pride.
But despite the trio’s success Cowley has downplayed his role in their development, and explained how the players should take credit.
He said: ‘Yes, of course (I feel pride). For us, I think we played a very small part in their pathway and we gave them the opportunity to play.
‘I’ll never be arrogant enough to say I made anyone a better player.’
Cowley was quick to implement his policy of acquiring hungry young players on loan at Fratton Park.
Alongside Azeez, Gassan Ahadme (Norwich), George Hirst (Leicester), Gavin Bazunu (Manchester City), and Hayden Carter (Blackburn) arrived temporarily this term.
Although they achieved varying success, Cowley described how he wanted to give them the platform to play.
He added: ‘For us, it was just trying to give them the confidence to play.
‘For Trevor, Emile, Miguel, Gavin, George, Hayden, and all these boys in the future – for us it’s just about creating a safe and secure environment, which allows them to play at their best.
‘I think particularly Emile and Trevor were able to do that, and it gave them lots of opportunity and experience which now has been a good stepping stone to what they’ve gone on to achieve this season.
‘The fact that both boys are so humble, I think says a lot about them. For sure, they’ll always have a special place in my heart.’