Rewind to 1992 and you’d find the world in a not too dissimilar position to how it is today.
Russia was politically unstable; the Californian city of Los Angeles was experiencing riots in the wake of the murder of Rodney King; and Glenn Pennyfather was rubbing shoulders with some of football’s elite in the inaugural season of the Premier League with Ipswich Town.
Fast forward to 2026, and Russia is still far from a stable state; political tensions and protests remain prevalent in the USA, and Pennyfather is still involved in the game he loves, but now commentating on one of his former clubs, Southend United.
Although he may not be a household name, Pennyfather’s career, both pre and post-playing retirement, is one that would leave many football fans green with envy.
After being scouted whilst playing with his mates by a member of his local community, he went on to enjoy a successful career, before later moving into management and is today working with BBC Essex.
Reminiscing on this he said: “I was at Fulham as a young lad, sort of 13, 14 years of age.
“Then one day I had a knock at my parent’s door and it was, would you believe it, a bloke from down the road who scouted for Southend United, and he literally ran one of the shops at the bottom of my road.
“There was a green where I lived in Billericay, which I played football on.
“He saw me there and he said, would you be interested in coming [to] Southend for a trial?”
Despite playing in an alien position during his trial, Pennyfather impressed and was one of a handful of players who were then offered contracts with the youth team.
“I went over to Southend and Frankie Banks was in charge who was a huge influence in my career,” he said.
“I went there as a right winger and I went in the trial game as a centre half, so that was great!
“There was probably 100 lads there at the time. I think I was one of three that Frank pulled out, and within a couple of weeks I was playing in the youth team in the Southeast Counties for Southend.
“I signed as an apprentice at 16 and I played in the first team when I was 17.”
Over 40 years later, Pennyfather is involved with Southend once again, working for BBC Essex, a career path he had always dreamed of pursuing.
“I always wanted to go in this side, in the media, the radio, presenting, that sort of stuff,” he said.
“It was Glenn Speller [who] asked would I go and summarise on the Chelsea game at Roots Hall, and I really enjoyed it.
“When I finished at Chelmsford, I got a phone call from Glenn, and 14 years later here we are.
“It’s great to follow Southend, my old club, all around the country.
“I’ve got my own show on a Friday evening on BBC Essex, the fans’ phone-in show, I enjoy talking to fans of all Essex clubs.
“I’ve been really lucky to be involved in football in different guises, as a player and as a manager and now as part of the media side, which I love.”
Pennyfather spent the majority of his career with Southend, making over 200 appearances during his six years with the Shrimpers.
During this time, he made lifelong memories with the club including promotion and a cup victory for the ages against one of the country’s biggest clubs.
“We had some fantastic times we really did,” he said.
“The standout, for me, was the Stockport County game away when we won up there to win the league on the Friday night.
“I got the first goal, Richard Cadette got the second, and we got promotion, which was absolutely fantastic.
“Beating Derby County as well in the League Cup,” he added.
“That was great because they had a team full of England internationals, Peter Shilton and Mark Wright, you know, regulars in the England team and little old Southend went and beat them.
“Roy McDonough got the penalty at home to Derby in the first leg and then we went to the Baseball Ground, and we put on a great performance and got the draw and we come away winners.”
The 14th century English poet Geoffrey Chaucer famously coined the phrase “all good things must come to an end”, and this can certainly be applied to Pennyfather’s time with Southend.
After joining the club as a boy, Pennyfather left as a man in 1987, aged 24, following consecutive seasons of consistent performances and was snapped up by Crystal Palace.
Former Southend United defender Glenn Pennyfather on his time with Sou… | TikTok
He loved his time at Selhurst Park, but Andy Gray rejoining the club left Pennyfather having to look elsewhere for gametime, with him finding a new home at Ipswich Town.
When with the Tractor Boys, Pennyfather won promotion from the second division, resulting in him starring in the inaugural campaign of the newly formed Premier League.
“I moved to Ipswich under John Duncan, again into a fantastic side,” he said.
“With players like John Wark, who had been top scorer at Liverpool for a couple of years previous, Chris Kiwomya, Jason Dozzell, Geraint Williams, who was captain for Wales at the time, Sergei Baltacha, who was the sweeper for Russia, Romeo Zondervan who was in the Dutch team.
“The Premier League was hard. I didn’t play too many games in the Premier League [because] I was blighted by injury quite a lot.
“I played in the quarterfinals of the League Cup against Sheffield Wednesday at Portman Road, and the pace of the game was unbelievably different, especially with the multi-ball as well.”
Pennyfather’s injury woes limited him to five top-flight appearances during the 1992/1993 season with Ipswich.
He then moved on to Bristol City, but continued injury struggles forced him into non-league with Stevenage and Canvey Island, before eventually an early retirement.
As a result, Pennyfather moved into management, an experience he enjoyed greatly.
“Absolutely loved it,” he said.
“My time at Canvey was a special time.
“We had a fantastic run where we went all the way to the National League, won the FA Trophy as well, just amazing times, amazing memories.
“We had great success there, and all sorts of successful things plateau out and come to an end, and it did in the National League.
“Jeff [King, Canvey’s manager] decided to call it a day, and we moved lock, stock and barrel to Chelmsford.”
He guided Chelmsford to high finishes in the sixth tier of English football, but promotion proved elusive.
Reflecting on his time with the Clarets, he said: “Jeff stayed the first year. We got promotion, and then there was a rejigging of the league, and we ended up in the National League South.
“I took over after that and had, I think, three goes at the play-offs, and we just couldn’t get it over the line and, unfortunately, that was it and my time in management and coaching came to an end then.”
Last month, Pennyfather turned 63 and ten days later he was back commentating from a cramped press box at Brackley Town, watching Southend run out 3-0 winners.
Now a resident of the Cotswolds, he continues to follow the Shrimpers up and down the country from Cornwall to Carlisle and will be hoping to be commentating on Southend playing EFL matches again in the not-so-distant future.
