The Emirates FA Cup trophy has made a special visit to Maldon & Tiptree, who are the lowest-ranked team in the 2025-26 Competition Proper. The club, currently topping the Isthmian League North Division, is preparing for a giant-killing mission this weekend as they travel to EFL League One side Port Vale in the First Round Proper.
The Jammers entered the competition at the earliest stage; the Extra-Preliminary Round back in August, and have won six ties on the spin to reach the First Round Proper, scoring 16 and conceding only three goals in that run.
Maldon & Tiptree got to the Second Round Proper for the first time in their history during the 2019-20 season, and followed this up by reaching the First Round Proper during the 2020-21 campaign, but with ambitious new owners and a talented squad, they’re aiming to go even further this time around.
The club was taken over by Barrie and Scott Drewitt-Barlow in February this year. Known for their success in business and television, the couple have assembled a strong team on and off the pitch, and the club has been reaping the rewards with formidable progress ever since.
The club was taken over by Barrie and Scott Drewitt-Barlow in February this year
The squad features former Celtic and Norwich City striker Gary Hooper, as well as Freddie Sears who was once of West Ham United and Ipswich Town. Their experience has proven invaluable – it was Sears who delivered the crucial moment in the Fourth Round Qualifying; a smart header that sealed a 1-0 victory over Flackwell Heath and booked a place in the First Round Proper.
Managing the team is former Manchester City midfielder Kevin Horlock. “It’s a big moment for the club and community,” Horlock said about the famous silverware visiting the ground. “To have this success and a day out at Port Vale is great for everyone connected with the club and hopefully we can go there and give a good account of ourselves. The competition has so much history – I’ve played in it myself, and to see the trophy and all the memories that come with it is brilliant. It’ll give the fans and players a real buzz ahead of the tie.”
While the club boasts some well-known names, many players balance football with their day jobs, and among the most remarkable stories from this squad is that of club captain Jack Cawley. Jack works as a London black cab driver, but when he’s not behind the wheel, he leads Maldon & Tiptree from the backline.
As well as captaining the side, Jack Cawley works as a London black cab driver
Jack’s connection to the Emirates FA Cup also runs deep. His father, Peter Cawley, was registered at Wimbledon at the time of the iconic 1988 Final win over Liverpool. Now, Jack is chasing his own moment of cup magic as the skipper prepares to lead the team out at Vale Park on Sunday.
“The FA Cup means a lot to me and my family”, Jack said. “To have the trophy not only here at Maldon & Tiptree, but in my cab, and on top of that, to be part of a cup run myself, is really special. It reminds you why you fall in love with football in the first place.”
Hundreds of staff, players, fans, and members of the community got to see the competition’s iconic silverware in person in the clubhouse before a recent league fixture. As the team prepares for one of the biggest games in their history, the whole town will be behind them.
Scott Drewitt-Barlow added: “The event summed up what Maldon & Tiptree is all about – community, ambition, and togetherness. Seeing the excitement on people’s faces as they had photos with the trophy was incredible, and it gave the players a real boost ahead of what is set to be a huge day for the club.”
Maldon & Tiptree face Port Vale on Sunday 2 November at 3pm GMT. The tie will be available to watch live on TNT Sports 1 and discovery+.
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