From failed Portsmouth trial to long-term deal with rivals Peterborough - how former Fulham and Reading man’s bounced back
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But there was to be no Pompey stay for Ryan De Havilland, when he arrived at the club’s Roko training base in the summer of 2021 after leaving Fulham.
The midfielder had come through the youth ranks at Craven Cottage after joining from Reading as a youngster, before his release.
Despite liking his technical ability, Cowley opted against offering De Havilland a deal - leaving him to drop down into the National League with Barnet.
It’s a step which has now paid off for the 22-year-old, after agreeing a lengthy four-year contract with Peterborough earlier this week.
Last season proved a breakout campaign for the Londoner as he banged in eight goals in 47 appearances for the Bees, culminating in play-off defeat to Boreham Wood.
De Havilland believes that experience has allowed him develop since Cowley ran the rule over him - and he’s now ready for what League One has to offer.
He told Peterborough’s official site: ‘I feel that I learned a lot during my time at Barnet. I felt that it was move that I needed, the physical side of the game I needed to improve on and I felt that my time in the National League has really helped me in that respect.
‘It is pleasing to get it all done right at the start of pre-season, I can now look forward to what is to come.’
Peterborough appear to be going through significant changes under Darren Ferguson after their play-off defeat last term, with a number of high-profile figures either on their way or set to depart.
Jack Taylor yesterday completed a move to the Championship with Ipswich - in the same department where De Havilland arrives.
Ferguson feels he has brought in a player with scope to develop under his guidance with the Posh.
He told the club’s site: 'Ryan is one we have known about for a while. He had a good upbringing at Fulham, he has gone down the pyramid to work his way back up again and that fits in with some of the players we have signed in the past.
'He has had a really good learning curve at Barnet and he has performed very well, we think we have a good player on our hands. He is a box-to-box midfield player, he has a good engine and he is both footed, which is very rare these days. His set-pieces were good last season as well.
'It is a signing that we are happy with, we are looking forward to working with him, he is a good age and has a lot of development in him. I think he will be a big signing for us, he will fit in really well.’