After retiring from football in 2019, Ashley Cole had no intention of leaving the sport and set his sights on management.
He became a coach at Derby County shortly after his playing career ended, and then went on to have similar roles at England, Everton and Birmingham City.
Cole, considered one of the greatest left-backs in football history, always had the ambition of becoming a manager and in March 2026, after nearly seven years learning his trade, he took his first head coach role at Italian outfit Cesena.
"The entire Cesena FC family is thrilled to welcome manager Ashley Cole to lead the Bianconeri first team and extends a warm welcome to him and his staff in Cesena, wishing them all the best of luck in this new adventure," said the club as they announced his arrival.
Verdict Given on Ashley Cole's First Month as Cesena Boss
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Cesena were eighth in Italy's second tier when Cole joined the club. At the time, they were on a seven-game winless streak, losing four and drawing three.
Cole had no desire to play the 3-5-2 formation Cesena had played throughout the campaign, instead introducing a 4-2-3-1. His reign didn't get off to a good start as they were beaten 3-0 by Mantova.
Tuttomercatoweb was scathing in their post-match report, calling it a 'terrible result.' They wrote: "Overly hasty tactical changes, considering the very short time they had to prepare for this match, meant his team struggled tremendously to build play.
"Cesena found themselves almost completely at the mercy of Mantua: a forgettable ninety minutes for the Bianconeri at the 'Martelli' and a terrible start to his coaching career for the former Chelsea player."
Corrierero Magna were also very critical as they questioned Cole's change of formation. They wrote: "The English coach should be granted some mitigating circumstances, such as the absence of several key players (Michele Castagnetti first and foremost) and, of course, the lack of time to make an impact.
"But it was precisely in this sense that Cole ended up triggering another short circuit: precisely because there wasn't time to coach consistently in the first week, what was the point of upending everything?"
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Cesena put the defeat behind them and managed to win in Cole's second match in charge as they beat playoff rivals Catanzaro, ending their eight-match winless run.
They followed that up with a 1-1 draw against Suditrol. Following that match, Corrierero Magna said that his management in the second half 'left some doubts', criticising Cole for taking Cristian Shpendi off early and saying none of his substitutions 'convinced or moved the game forward'.
In Cole's most recent match, Cesena were beaten 2-0 by Juve Stabia. Tuttomercatoweb were again critical of Cole following the match, handing him a 5/10 rating. They wrote:
"'His' Cesena is struggling to find an identity and, above all, consistency. Too many inconsistent performances since his arrival on the Romagna bench: watch out for this defeat, because it risks complicating the playoff race..."
As things stand, Cole's side are currently in eighth position with four matches of the campaign to go. They need to finish in the top eight to qualify for the playoffs.
Ashley Cole Reveals How Much He Struggled to Land a Job in England
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Cole has revealed he tried to get a head coach role in England, only to be 'discouraged by a lack of opportunities'. He said:
"I was getting kind of discouraged by a lack of opportunities, from some clubs in England I spoke to. They like to throw the 'you don't have experience' line. And I'm like, I get what you're saying, I agree - but how am I going to get experience?
"That's the battle you have to fight as a number two for six or seven years - you have to take a leap of faith, but a club also has to take a leap of faith."
Cole also said he was 'very proud' to be managing Cesena. He continued: "I don't think there are too many black English coaches working in Italy, so yes, it is a massive leap of faith from them and I'm very proud to be here. It is a great place to be and to start. I'm glad I'm back. We're going to do something different - a bit special."