'When you’re winning and you hear ‘We are Sailing’ you wouldn’t want to be anywhere else' - Jamie Grimes on his time at Chesterfield

This summer marks the start of a new chapter for Jamie Grimes when he moves on after five years and 191 matches with Chesterfield.

Just recently week the man who captained the Spireites to the National League title and led by example countless times sat down and reflected on his time at the club, from the challenges of waterlogged training facilities at the start to being at the centre of a resurgent club he helped pilot back to the Football League.

Here are some of the highlights of the conversation with 1866 Sport’s George Parr.

Choosing Chesterfield

Career high: Jamie Grimes celebrates after scoring Chesterfield's first goal against Boreham Wood that helped take the club back to the Football League. Photo by Cameron Smith/Getty Imagesplaceholder image
Career high: Jamie Grimes celebrates after scoring Chesterfield's first goal against Boreham Wood that helped take the club back to the Football League. Photo by Cameron Smith/Getty Images

"When I left Swansea I wanted to go and play at a club with a lot of fans.

"When I first signed there were 4,500 to 5,000 people watching us. The support just got better and better and that comes with performances on the pitch and the standard of football getting better and better.

“When you’re playing in front of 8,000 to 9,000 it’s special. There aren’t many moments you get to enjoy but when you’re winning and you hear ‘We are Sailing’, you wouldn’t want to be anywhere else.”

Humble beginnings

Skipper Jamie Grimes in amongst the supporters. Photo: Cameron Smith/Getty Imagesplaceholder image
Skipper Jamie Grimes in amongst the supporters. Photo: Cameron Smith/Getty Images

“When you look back to 2021 and the standard of the team, the standard of the facilities, the standard of everything, the club do is just chalk and cheese, it’s gone through the roof.

"The first time on the training ground you couldn’t train on it for much of the year. It was waterlogged, muddy.

"It wasn’t a good environment to train at the top level but now, with the help of the Kirk family, the training ground pitches are top notch.

"Buildings are going up and it will be amazing when it’s done. The club is going only one way.”

Playing against Chelsea in the FA Cup

"My first memory was during the warm-up. There were two tiers in the away end at Stamford Bridge and it was just a wall of Chesterfield fans.

"It was so loud we couldn’t hear what Jordan Hardy (sports scientist) saying. That was Spireites on tour. That’s when I first realised this was a big club and it was where I wanted to be.”

Losing the 2023 National League play-off final at Wembley

"To be winning and then concede late on and lose on penalties was gutting. But losing that game galvanised us.

"A lot of the players stayed and we had about three weeks off and we came back to pre-season flying.

"We didn’t start the next season the best in terms of football but late on in games were were winning 3-2 and 4-3. You knew it was going to be a magic season because everyone was on it.”

… And going up the following year

"I’d never scored two in a game and never won a league title but I did it all in one day when we beat Boreham Wood. It was probably the best moment of my career.

"We were never going to lose that game. We’d gone to Halifax on the Wednesday night and played on a mudbath and lost. One of their players was doing a trophy celebration to the fans.

"We were sat in the dressing room (a few days later) knowing we weren’t going to lose. It was like a dog on raw meat.

"After the win we were celebrating until Monday I think.”

Regret

“The first season back in the EFL when I had that little injury in pre-season that put me down the pecking order. I wish I’d done things differently, maybe not worked so hard, but I went at it harder because I was thinking ‘I’m in the Football League now. I have to be better.’

“My body told me you can’t do triple sessions. You have to cool down a bit.

"I did still manage to play a lot of games and it was good for the football club to be back in the league.”

Community work

"I would have done it even if I hadn’t been captain. I’d always make time for things.

"I try my best to get players to go places and they’ve been good for me in that way.

"The people on the community side work so hard to make that interaction.

“At the end of the day there is more to life than football, but we love the club because of football.

"The longer you spend at the club the more you realise it is all about the community.

"If you lose the fans are passionate about the losing. If you win they’re passionate about the winning.”

From non-starter to Man of the Match

“I got the Man of the Match against Notts County on Boxing Day and the reaction from people was really nice.

"I needed that because at that time I was really frustrated, as every footballer should be if they’re not playing.

"Be frustrated, but do things the right way and work hard.

“I got my chance through injuries and there was no way we weren’t winning that game. I was so so hungry.

"To reminded you are loved and you can play was special for me.”

Going out on loan

"The emotional time for me was when I left on loan (for Boston in February) because that’s when I knew my time was up.

"The gaffer was good to me. He told me nice and early I was done. He had me gather with the players in the dressing room and everybody said their goodbyes.

"After that I just wanted the lads to win at Wembley to see the season out.

"It was disappointing to leave but all good things come to an end.”

Wearing the armband

"It was an honour to captain the club over the five years. I know it’s a cliche but when you leave a club you want to leave the shirt in a better place. I feel it is in a better place.

"I’m a small cog in a big wheel and every day I came in I wanted to be better. We went from National League, play-offs every year, and now the club is going only one path.

"I think the expectation is it will do well and go up again. I think this club deserves at least League One.

The future

“I’ll always be a Spireite. Wherever I go I think I’ll always be following them. I was like that this year at Boston after a game, asking ‘how did Chesterfield get on?’

"I want the best for the club because the club has done the best for me, from the gaffer, the chairman, the fans etc. Everyone was done so much for me to achieve my dream of going back into the Football League.

"I’m sure I’ll be back watching games when I can.

"I’m doing my coaching badges so I’ll try and get in and do a few coaching sessions with the kids and give a little bit back. I’m a lifelong Chesterfield fan now and I’ll do anything for the club.”

News you can trust since 1855
Follow us
© 2026 Iconic Media Group Ltd. All rights reserved.Cookie SettingsTerms and ConditionsPrivacy notice