20 Questions: Colchester United

U’s fan Dean Bennell describes life following a lower league club that have never been to the new Wembley and haven’t been promoted for nearly 20 years

Jun 24, 2025

Tuesday 24 June 2025

If you’d like to write an article for The Scarf My Father Wore, share a few snippets or photos, or advertise your business, please email thescarfmyfatherwore@substack.com.

THE SCARF MY FATHER WORE 2025-26 CALENDAR: Having been to all 56 County games this season, I’ve taken thousands of photos. I’ve put together calendars for next season, featuring some of my favourite photos from the last year, plus some other County bits and bobs. £10 each. Get in touch if you’d like one.

Dear County fans, Stopfordians, Colchester supporters, and anyone else from The Football Family joining us today, a very warm welcome to your Tuesday edition of The Scarf My Father Wore.

To an outsider, it seems pretty grim being a Colchester United fan. They play in one of the most soulless new builds in the country, and haven’t been promoted for nearly 20 years. It seems Colchester fan Dean Bennell would actually agree with me – just look at his answer below describing his football club as a TV show. There have been some great moments over the years though, which Dean discusses today, such as beating Leeds in the FA Cup, winning promotion to the Championship, and putting seven past Norwich on the opening day.

Dean also runs his own business in Colchester. He’s a whole of market, independent mortgage adviser with nearly 10 years experience across all residential and buy to let areas. If you require his services, give him a call on 07521 080562 or email dean@jmbltd.co.uk.

Today’s edition is sponsored by Colourtone. A big thank you to Paul.

Finally, I’m currently walking every street in Stockport to raise money for mental health charity Mentell. If you’d like to make a donation to help me reach my target, please click here.

Total distance so far: 253.75 miles

Total steps so far: 418,084

Total raised so far: £2,312

Total completed streets so far: 474 (Click here for the full list, which includes reports and photos from every day of the walk.)

Further information on the walk can be found by clicking here.

Des Junior

Leave a comment

Photo credit: Colchester United FC

Colchester currently play in League Two, which is the fourth tier of English football. What’s that like as a division?

A tough division with not a lot between most of the clubs. Each season you wait and see what happens over the summer transfer window and who builds the best squad. To some extent it makes it an exciting league as it really can be quite unpredictable each year but being a Colchester fan it has become very boring. The same cycle of teams and away days every year and a lot of stress hoping that we aren’t going to be fighting relegation again, but as of last season things are on the up.

Describe a typical matchday for yourself in Colchester.

Head to the local pub with some mates for lunch and drinks. Talk about the football and put some bets on. We sometimes have personal bets between us as well. Head to the ground in time for kick-off.

Who are your club’s biggest rivals?

Southend United. It’s been great seeing them struggle to get out of the National League. All they go on about is their attendance. Slight disappointment not seeing them come up in the play-off final as it would have been good to have the rivalry again.

What’s your best memory following Colchester?

Our promotion and two seasons in the Championship were special, the second of which was our final season at our old ramshackle ground Layer Road.

Best individual memory? Beating Norwich 7-1 at Carrow Road on the opening day of the season in League One. Just a shame it got tarnished by them taking Paul Lambert from us then beating us 5-0 at home!

What’s your worst memory following Colchester?

There are many but the most recent is watching us lose 5-0 at Forest Green two seasons ago. That game really felt like a low point and you felt like we were heading towards the National League after that. Captain Connor Hall arguing with fans live on Sky – total headloss from everyone.

If Colchester United was a TV show, which one would it be?

Probably something like EastEnders. 99% drama and misery.

What’s your ground called, and how would you describe it for someone who’s never visited before?

The Colchester Community Stadium, currently known as the JobServe Community Stadium. It’s a basic, identikit modern stadium without much character. It’s comfortable, so you’ll get a good view of the game. Positives are there are loads of parking options nearby with different food and leisure facilities next door.

What’s your thoughts on Stockport County?

Solid club. I do have admiration for them after being in non-league for so long and then climbing and establishing themselves solidly in League One. Despite having a financial backing it’s a club that’s not sold its soul and seems to do things properly. Played very good football in the League Two promotion season.

Have you ever visited the town of Stockport before?

Stockport away is unfortunately still on my to-do list!

What colours do you play in, and what’s the best ever kit Colchester have had?

Blue and white stripes, although our owner had us in plain blue for a couple of seasons. I loved our 2004-05 Admiral home shirt, with the 1993-94 Spall home shirt a close second.

If Colchester were playing in the next FA Cup final, who’d be at Wembley as your celebrity fan?

Our celebrity fan has always been a radio DJ called Steve Lamacq. However, we’ve had new professional boxer Lewis Richardson at the stadium a few times since his Olympic medal win.

What’s the most interesting fact about Colchester United we might not know?

Probably us beating Leeds United 3-2 in the fifth round of the FA Cup in 1970-71. Don Revie wasn’t best pleased.

Who’s your all time Colchester hero?

I think my all-time hero would be Jamie Cureton from my childhood years. What a striker!

What sort of attendances do you get, and how would you describe Colchester’s fanbase?

It’s a small but loyal fanbase. Our attendance has increased to an average of 5,000 over the last two years, mainly due to some excellent matchday work from our voluntary fans group Blue White Army and the positivity that the Cowley brothers bring to the club.

What’s your manager like?

Danny Cowley is the kind of manager you absolutely love, but would hate as any opposition fan. The Cowley brothers are excellent man managers and they do all the simple things perfectly, focusing on the club as a whole rather than what’s just out there on the pitch. We were told to expect anti-football from them by opposition fans, but we’ve been playing some really nice possession based football most of the time.

What’s your owner like?

Robbie Cowling took over our club and has unfortunately been a divisive character. Over the years the club has lost its community feel and the matchday experience has died down. I believe he has the club’s best interests at heart but some stubborn decisions over the years have cost us, although it does feel like he’s changed direction with his recent budget choices and appointment of the Cowleys. We’re currently going through takeover talks with an American consortium which has been welcomed by most clubs. New investment and passion would do wonders for our club and probably see us kick on up the leagues.

What’s it like for a night out in Colchester?

Plenty of options in the town centre with a couple of clubs and a lot of bars and pubs, including chains like Walkabout, Yates, Slug & Lettuce. We have a popular games bar as well. Busiest night is a Saturday, but it’s got quieter over the years. If you come from a town with not much to do then Colchester would be a good option for sticking around post-match compared to a number of other League Two teams.

What’s the best thing about being a Colchester fan?

I think it’s being proud to support your local team. Twenty minutes north of us we have Ipswich Town and a great deal of Colchester residents have ended up being Ipswich fans. Forty minutes south we have West Ham and routes in to other London clubs too.

What’s the worst thing about being a Colchester fan?

Being one of the few clubs to never play at the new Wembley, being one of the clubs to go longest without a promotion, and being accustomed to always having one eye over your shoulder at the League Two relegation zone even if you’re playing well!

What are your hopes for this season?

To have another solid season that’s a bit more consistent and potentially be sniffing around the play-off spots again. Last season was a huge step forward for us, despite the disappointment of falling just short of the play-offs.

➡️ Enjoyed today’s article? Click here for all of the other ‘20 Questions’ features we’ve published.

Give your car a lick of paint

Granted, Stockport used to be a little rough around the edges. But the town’s getting a good old lick of paint these days, with fancy new offices, apartments, bars and restaurants springing up. You can’t be driving up and down the A6 in a tatty car with chipped paintwork, so give your car a nice lick of paint too. Colourtone is your go-to company for that. They’ve been servicing the automotive and industrial markets in Cheshire and Greater Manchester for decades, and carry an extensive range of car paint and industrial paints.

➡️ Visit colourtone.com for further details.

Photo of the day

Colchester Community Stadium

County won 2-1 on their last visit to Colchester, on an emotional night in April 2024, to leave themselves needing just one point to clinch automatic promotion to League One.

5 questions with Dean Bennell

What’s been the best moment with your business so far?

I think having my first customer complete on their first house purchase as a self-employed adviser was the best moment. They came to me with zero expectations of being able to buy a house and within six weeks they had the keys.

What’s your plans for the business in the future?

Most people talk about growth and employing other people etc but my five year plan is to establish myself whilst keeping my customer base small so I can service everybody to a high standard. I don’t want to start employing other advisers underneath me and losing that relationship I have with my customers.

What would you like to promote to The Scarf My Father Wore readers?

I’d like to promote the fact that I am a whole of market adviser, completely independent, and the fact that I genuinely charge no fees for my services. The fact I have no overheads means I can keep that promise and give customers the best service without it hurting their pockets.

Kirstie Allsopp said young people should cancel their Netflix and gym memberships if they want to buy a house. Do you have any better advice for any of our younger readers wanting to get on the property ladder?

Educate yourself as much as possible around mortgages and speak to independent mortgage brokers. There are a lot of things out there that can help you. The hardest part is raising a deposit. You have mainstream lenders like Accord Mortgages and Skipton Building Society providing sub-5% or 0% deposit options. Lenders like Santander would allow you to take a personal loan to fund your deposit, instead of savings. If you like new build, a lot of developers can help boost your deposit with cash incentives as well. There are lots of things out there and the best advice is to speak to someone who can guide you. If you aren’t ready to buy now, we can certainly build you a plan and give you something to aim for.

What’s the best thing about living and working in Colchester?

Obviously it’s living next to League Two’s mighty U’s. I don’t know why anyone wouldn’t want to live here!

➡️ Looking to buy a house at the moment? Give Dean a call on 07521 080562 or email dean@jmbltd.co.uk to see how he can assist you.

Today in SK

🎬 Cinema

Two films at The Savoy Cinema (SK4) today. The Salt Path (12A) at 5.30pm, followed by Mission: Impossible – The Final Reckoning (12A) at 8pm. Click here for tickets.

🍻 Food and drink

The Nelson Tavern (SK1) have a great range of offers throughout the week, including £5.50 for drinks off the Doubles Bar, a comprehensive range of shots for £1.50, and 3 for £7 on Jägerbombs. Also, double up for £2 on premium spirits.

Bitter £2.30 a pint all day at The Cross Keys (SK8). Plus, discounts on certain lagers till 6pm.

If you’re heading out for a few beers today, pop into one of our featured venues such as The Crown (SK2), The Dog & Partridge (SK2), The Crown Inn (SK6), The Three Tunnes (SK7) and Flute & Firkin (SK12).