After more than five years at the helm of Dulwich Hamlet, Ryan Marvin Dempsey has stepped into a new challenge as Assistant Manager to Tom Davies at Cheltenham Town. The move comes as the club makes an impressive start to life in the third tier, with three wins from their opening four matches.
Dempsey’s football journey has been anything but conventional. “I grew up in Braunton, North Devon, it’s a beautiful place to live, which I appreciate now, not as much when I lived there,” he reflects. A Liverpool supporter with family ties to both Liverpool and Stockport, Dempsey also keeps an eye on Fulham results after spending five years working for the London club. His coaching career has been diverse: “I think I’ve worked within every coaching environment to date — grassroots, male, female, academy, education, disability, health, U7s to adult. It’s been a journey I’ve been proud of so far, and one I’m looking forward to creating more memories and achievements in the next few years.”
The decision to leave Dulwich Hamlet was not one Dempsey took lightly. “I thoroughly enjoyed my time at Dulwich. I was there for five and a half years and made some very good friends, and I will always miss certain elements of the club and the people who make it a special place to work,” he says. “For me, I felt I needed some time to try and recharge, take a step back. Although most job roles within football are part-time, it’s never just part-time.”
What started as a plan to observe other clubs soon turned into something more. “I had met Tom during a couple of courses, and we always kept in touch. I spoke to him about coming and observing some sessions, and he said yes. A couple of weeks later, he called me back and said there was an opportunity to join Cheltenham — and after I thought about it, it was an opportunity I couldn’t turn down.”
Transitioning from manager to assistant came with an adjustment period. “It was strange at first,” Dempsey admits. “However, Tom has been brilliant with me — he hasn’t got bored with me asking lots of questions yet! I think it’s really important to have a good relationship between the manager and assistant. The most important part for me is that, similarly to my relationship with my assistant Jamie while at Dulwich, I feel valued. Tom asks my opinion and thoughts on everything, but ultimately, the manager has the final decision.”
The role has eased some of the pressure of management while still keeping him fully engaged. “There’s less pressure on me; I’m involved in all of the discussions, but I don’t have to make the final decision. I suppose I’m the link between the players and manager once that trust is established. I don’t approach it any differently; I still think as a manager and hopefully that helps.”
Logistics also played its part in the transition. “Pre-season was tough as I was still living in Croydon, so the six-hour round trip was difficult to manage, but it has been well worth it. My family has moved to Bristol, so the distance is pretty easy to manage,” he explains.
On the pitch, Cheltenham have quickly recovered from an opening-day defeat against Exeter City to win three straight matches. Dempsey credits both pre-season work and the squad’s mentality. “Pre-season is always a challenge as players are on holiday and recruitment is getting more competitive with the budgets available in tier 3 and 4. Saying that, we went unbeaten during pre-season, which was pleasing. Going into the Exeter game, we were expecting a tough encounter but were confident in getting a result. We had a couple of good chances in the first half and then conceded two poor goals from our point of view to lose the game — but it was a performance that gave us hope and belief moving into the next set of games.”
With eight new players bedding into the squad, chemistry is still developing, but Dempsey has been impressed by the qualities shown. “Winning the last three games, we have witnessed what’s needed to win games of football: work ethic, desire, belief, throwing their bodies on the line (which they showed in abundance to beat Oxford United 1-0), and quality in both boxes. There are always areas we want to improve, and the most important aspect to achieve improvement and development is that the players are fully committed to doing so.”
Having now experienced both Tier 3 and Tier 4 football, Dempsey has noticed key contrasts. “One of the main differences I have noticed in my short time in Tier 3 is in players’ decision-making and technical ability to keep the ball. There also seems to be more accountability and honest feedback between the players; they check and challenge each other during training and games.”
Looking ahead, Cheltenham’s targets remain grounded but ambitious. “The goals for the season are to be better than last season. Can we finish higher in the league? Can we get to the fourth Round of the FA Cup? Can we win trophies? All we can do is enjoy working hard, improving and playing with smiles and win games. If we do that, I’m confident we can get to where we want to.”
The immediate focus, though, is the FA Women’s National League Cup group stage, where Cheltenham face Birmingham City’s Academy side. “I’m a fan of the new-look FA WNL Cup Group stage. It will be a good test against a PGA team,” says Dempsey. “It’s always a good challenge; it’s an opportunity to rotate players and ensure that everyone gets opportunities to challenge each other. As always, we will continue to concentrate on our own game model and how we want to play. It’s an opportunity to play and perform to our maximum potential to win the game.”
