Former Old Gold midfielder Simon Osborn reflects on his most elegant, skilful and stylish teammates, kits and moments which make up his beautiful game.
Most beautiful player | Ian Wright
I was fortunate to play with Ian Wright when I was at Crystal Palace and Wrighty scored some amazing goals, and had some unbelievable talent, so he was probably the best player who was my teammate. But I also got to play against some incredible players. I was also fortunate to play in the Barcelona game at Molineux against Figo, who was an outstanding player, but I also have to mention Gazza, who at the time in the early 90s, before he picked up his knee injury – and even after that, to be fair – was an unbelievable player.
Most beautiful Wolves teammate | Gordon Cowans
There are probably two players who stand out for me. When I first got to Wolves, Gordon Cowans was at the club and he had obviously played at the highest level, played for England, played in some really big games, and whatever else, so he was technically very good, two footed and a really, really talented player. Then later in my Wolves career, Robbie Keane came through, who was one of the best young players of his era. They were the two that stood out to me, because Gordon, being a midfield player like myself, was someone I looked up to, and Robbie too. Another player who was underrated and probably wouldn’t get as much said about him was Temuri Ketsbaia. He was an unbelievable footballer, if we’re talking technically. He had incredible technical ability, you wouldn’t know what his better foot was, but he was obviously a bit of a livewire!
Most beautiful opposition | Arsenal
I would say playing against that Arsenal team in the Viera era. Fortunately, in my career, I was lucky to play a little bit against some of the best players in the country at the time and we played Arsenal in the FA Cup and they had the likes of Pires, Henry, Viera, Kanu – players like that. They were an unbelievable team at the time. But in the Championship, the Fulham team under Jean Tigana was an amazing side with the likes of Louis Saha, John Collins, Lee Clark. I’d say they were probably the best team I ever came up against in the Championship. When we faced Arsenal, we were a Championship side going up against one of the favourites for the FA Cup, so it’s not like you’re expected to get a result, you just try your hardest to hang in there and try to win your individual duels, compete a best as you can, and see where it takes you, but it’s not easy.
Most beautiful kit | Wolves 1998-00 home
It wasn’t one of the Wolves home ones with the deep neck on the collar! I quite liked the blue away kit in the early 2000s, that was a lovely kit, but the gold and black home Goodyear kits that I had in my first season and in the later 90s were very good. I would say they were the two that I liked most. We sort of went a bit funky with the colours of the away kits with the whites and the greens which I didn’t like as much, as well as the low cut collar on the home kit, which I didn’t particularly like either, so I would say the 1998/99 home kit and the early 2000s blue away kit were my two favourites.
Most beautiful goal | Taylor vs Gillingham, 2003
I’ve seen a few great goals. There are a few of my own which I quite enjoyed. I scored a volley away at Fulham for Wolves, but one of the best goals I’ve seen scored at a game I played in was against me when I was at Gillingham and we were playing against Portsmouth and I think it was Matt Taylor who hit a great volley. But he scored some cracking goals at that time.
Most beautiful stadium | Wembley Stadium
I always liked playing at Highbury. It was a tight ground, a beautiful pitch, and that’s one of the reasons, why I have memories of that, but also Old Trafford back in the day was a great place to play at, and then I was fortunate enough to play at Wembley. I would say that playing at Wembley was the pinnacle of my career, and to be able to play at Wembley was always the dream. Growing up watching the FA Cup, it was a special day and it’s a lot different to what it is now, with the whole build up to the day, but being able to play in the play-off finals at Wembley was amazing. Although it wasn’t a big pitch, there was an incredible atmosphere, and getting to experience coming out of the changing rooms and through that tunnel at the corner of the pitch was just a great experience.
Most beautiful moment in history | Making debut at Anfield
For my own moment, it would be making a professional debut for Crystal Palace. It was one of the biggest moments of my life. I was lucky enough to make my debut at Anfield alongside the ex-England manager Gareth Southgate. We both made our debuts together for Palace at Liverpool, so it was amazing to be able to do that. Then my second moment would be scoring my first ever goal, which was in the old First Division against Norwich. They were two standout moments for me, because it’s the result of everything you’ve been working so hard for your whole life coming to fruition. You work so hard to become a pro, so to get your full debut and then to actually score are moments that you’ll never forget.
This article originally featured in Wolves' official 2025/26 matchday programme. Last season's programmes are still available to purchase online through retailers Curtis Sports.
