19th April 2026

Saturday’s game against Jersey Bulls was a milestone 300th game appearance for marauding wing back Jack Penny.

It began with a conversation in a pub with Kingy.

Born in Scotland in 1997, his first word was “ball”. When he was three years old he moved down to Kent and grew up in Broadstairs, where he still lives. Penny started football in the youth set up at Ramsgate before he made the switch to Deal following a conversation with Kingy by the pool table. Jack graciously was prepared to put his annoyance of not being picked by Kingy for Kent school trials behind him and sign for the Hoops.

Penny is a forward thinking left back who likes getting up and down the wing. Penny recounts: “When Kingy actually signed me he said he was going to play me as a number 10 not as a left back. I played most of preseason there and then he pulled me back. I like where I play now but I think it’s the way that we play which makes it easier. I wouldn’t like playing more defensive, and in fact, I wouldn’t be much good at just staying back and sitting there.”

Despite many attempts to score from corners this season, he still favours setting up the goals rather than scoring them. “Assists, definitely,” he says. “I’d take that over a goal.”

Non-League Roberto Carlos? Non-league Trent Alexander-Arnold?... “more like non-league Leighton Baines” jokes Jack.

Penny has become a mainstay of Kingy’s sides over the years, and he has built a great relationship with the Hoops manager. “We’ve got a bit of love hate relationship me and Kingy. I have a sore left ear most of the time! I’m quite pleased when we swap sides at the start cos then I know I get 45 minutes of peace! It’s what works for us I wouldn’t have it any other way. It doesn’t work when someone tells me I’m good all the time!”

Looking back on his highlights in his career at Deal. Jack looks back fondly on Whitstable and Faversham away wins in the SCEFL title winning season. “Once we got out of that game, we realised we had beaten the team that everyone fancied. It was a great result and a great memory of the team. The feeling of being near enough home and hosed after Whitstable was great.”

Off the pitch, Jack works on the railway and by his own admission doesn’t particularly enjoy training; “I hate it,” he says, bluntly. “If there’s a game instead of training, I’m happy.” Pre match, Penny is the club’s dressing room DJ, getting the team ready for kick off. Music choices have received mixed but largely positive reviews from his fellow players. “It’ll go from country to rap. Then house music to some geezer doing acappela. Sometimes they like it, sometimes they moan.” says Jack.

A regular. A creator. A DJ. A 300 game Hoop.

Congratulations Jack.

Tagged: Jack Penny