The 2025/26 League Two season for Cheltenham Town Football Club proved to have no shortages of ups and downs, from lurking in the depths of the relegation zone to guaranteeing League Two football next season with five games to go.
A feat achieved by the very man who got Cheltenham into the Football League in the first place.
In this article, we will look at how the season played out for Cheltenham, how they can build upon this season and some personal individual awards for Town players.
The Robins had a less than desirable start to the campaign, failing to win a game in the league for six matches with victory finally coming in the seventh.
Michael Flynn would be sacked after a 0-3 defeat at home to Oldham Athletic, ultimately unable to recapture that magic that helped stabilise the club following their relegation from League One in 23/24.
Some fans argue that perhaps Flynn caught most of the flack and it was those appointed above him who sold him down the river, and there is some truth to that viewpoint.
The 30th of September 2025 would see the return of former player and gaffer ‘Super’ Steve Cotterill, the man responsible for putting Cheltenham Town FC on the map.
The benefits were felt almost immediately, lifting both the spirits of the players and the fanbase with results changing in the blink of an eye.
Cheltenham would beat Fleetwood Town 2-0 at home to kick off Cotterill’s second stint as a Cheltenham Town manager.
Big wins came against the likes of Salford, Newport County, Bristol Rovers, Swindon Town and Walsall; who were then top of the table followed and soon genuine belief emerged that Town could stay up.
The ascension would be completed and Cotterill would secure mathematical safety in a 0-4 away win against Walsall to keep Cheltenham Town FC a Football League club.
Isaac Hutchinson (POTS) – Every Town fan, or even League Two fan, would have guessed this a mile off but Hutchinson’s season has been nothing short of outstanding.
Arriving to Cheltenham on loan from local rivals Bristol Rovers for which Hutchinson had varied game time, the move presumably was a way for him to return to that form that secured him the move to Rovers in the first place.
Hutchinson took like a duck to water, scoring an unbelievable free kick in the second minute to secure Cheltenham’s first league win of the campaign against Accrington Stanley.
He would continue to grow from strength to strength, moving into double digits for goals scored. At the time of writing, Hutchinson sits on 16 goals in the league with three assists and those statistics have earned him a spot in the 25/26 League Two Team of the Season.
Hutchinson has proved his quality working under two managers this season and maintaining his impressive goal contributions throughout.
Despite the recall from his parent club earlier in the season, Hutchinson has conducted himself well and remained professional throughout; proving that a player can produce their best stuff when thriving in a happy environment.
Jonathan Tomkinson (YPOTS) – The American has been somewhat of an underrated player this season, often going under the radar but consistently producing 5/10 performances minimum.
Additionally, Tomkinson has played in 33 games this season and started all 33 averaging 89 minutes per game.
His only goal for the season so far has proved to be massive, scoring the only goal against Bristol Rovers in a 1-0 home win.
Tomkinson has been loaned out a few times during his early career, but it appears that he might have found a permanent home in Cheltenham.
Evidently trusted by Cotterill and the fans, Tomkinson deserves his flowers even if the performances at times have not been the flashiest.
He has worked hard to make himself a platform to build upon into next season – earning his rightful spot in the team.
One reoccurring issue for the Robins this season has been conceding goals and an abundance of them at that.
Cheltenham have conceded 71 goals so far this season which is the fourth most conceded in the league, behind Tranmere, Newport County and Barrow AFC.
While Cotterill has addressed this issue with recent games often going into half-time goalless, it’s important this team has that approach to games from the start of the 26/27 season and not as late as it has been this season.
Another improvement would be nailing down a ‘full-time’ keeper and moving away from current Robins goalkeeper Joe Day.
Day has saved (pardon the pun) Cheltenham multiple times this season, but the 35-year-old will want to have a lighter schedule, especially given that he originally signed as a player-coach.
His expertise could help improve the game of another permanent goalkeeper in addition to developing an 18-year-old youth prospect in Mamadou Diallo.
Much of what has been seen of Cheltenham in recent months suggest the improvements are already being made as we speak and it is more the finer details that need fine tuning.
Whatever happens, Cheltenham Town FC are in safer hands with Steve Cotterill at the wheel.
