Bob McNab was a double winner in 1971, Sammy Nelson won the FA Cup in 1979, Kenny Sansom captained the side to the League Cup victory in 1987. Cole, of course, has won the lot. However, the best of them all was probably a fuzzy-haired Brummy who was a late starter in league football.
He had spent the early part of his career not getting a game at either Birmingham City or Oxford United but it was under Dave Bassett at Wimbledon that he began to build a reputation as a combative left back.
Perhaps not as technically gifted as others, Winterburn was instead a grafter who never gave less than 100%. So much so in fact, that he was voted fans player of the year in each of his four seasons at Plough Lane.
His early time at Highbury was not exactly a success. He spent six months in the reserves as under-study to the great Kenny Sansom and when he did finally get a chance in the first team, in December 1987, it was in an unfamiliar right back position.
It was in this position that he was involved in two incidents which put him in the spotlight in the early part of 1988. The first was in February in an FA Cup 5th round tie against Manchester United at Highbury. After missing the last minute penalty that sent Arsenal through 2-1, United's Brian McClair was openly mocked by Winterburn in front of the North Bank.
To this day it is unclear why he did it or what was said, but it clearly made a lasting impression on McClair and no doubt was behind the Scotsman landing several kicks in Winterburn's back during the now infamous brawl of Old Trafford two and a half years later. Perhaps this is where he earned the nickname 'Nutty Nige.'
It was another missed penalty, in April 1988, that would lead Winterburn to want to kick himself. After a series of missed spot kicks throughout the season, Arsenal had nominated Winterburn as the new penalty taker in early 1988 but they were not awarded another kick until the latter stages of the League Cup final at Wembley against Luton Town.
Leading 2-1 at the time, Winterburn knew if he scored the cup would be Arsenal's for a second year in a row, but his well struck penalty was saved by goalkeeper Andy Dibble and Luton came back to win 3-2.
However, Winterburn was build of stronger stuff and he came back better than ever. After Sansom left for Newcastle in the summer of 1988, he became the first choice left back for the start of the 1988-89 season. It was a position he would keep for the next 12 years.
As part of the famous back four alongside Tony Adams, Steve Bould and Lee Dixon, Winterburn would win 3 league titles, 2 FA Cups, 1 League Cup and 1 European Cup Winners Cup with the club. And he never let his performance levels drop.
In all he played nearly 600 times for the club, 4th in the all-time list behind David O'Leary, Adams and Dixon. The only surprise was that he won just 2 England caps, often below the likes of Tony Dorigo and Graeme Le Saux in the pecking order as under-study to Stuart Pearce.
But he was one of the first names on the team sheet at Highbury, firstly under George Graham and then Arsene Wenger. There was a brief period during the Bruce Rioch season in 1995-96 when Winterburn felt his days at Arsenal might be numbered, but the arrival of Wenger in 1996 gave his career a new lease of life.
Coming up to 33, many felt Winterburn's time at the club was coming to a end but he would be a regular in the side for the next three and a half years and helped the club to the Double in 1998.
That proved to be his last trophy success with Arsenal. By early 2000 he had lost his place to Brazilian Silvinho and at the end of the 1999-2000 season he left Highbury for West Ham.
Winterburn would play on for another two and half seasons at Upton Park before retiring in February 2003 with over 850 career appearances to his credit.
When looking for role models, young footballers these days probably turn their attentions to Cristiano Ronaldo or Lionel Messi but they would do well to follow the example set by Winterburn.
Lacking the natural gifts of others, Winterburn showed that there is no substitute for hard work and application, and a look through his medal collection shows just what can be achieved.
I was a regular at Highbury throughout the 1990s and it was great time to follow the club. We saw some truly great players such as Dennis Bergkamp, Ian Wright, Tony Adams and Patrick Vieira. But one of my favourites would have to be Mr Consistency.
He gave us so many great memories. The crunching tackles, the unusual puffed-out-cheeks running style and some spectacular goals. The right-footed effort against Wimbledon as we closed in on the 1989 title will never be forgotten. And what about the winner at Chelsea in 1997?
It was easy to take Winterburn for granted. He was just always there. He rarely had an outstanding game - I cannot remember him getting man of the match award for example - but he never had a poor game either. He was a 7 out 10 every week without fail.
I may be biased as I grew up watching him, but if I had to select my favourite English player of all time it would probably be the fuzzy-haired Brummie.
Nutty Nige, I salute you.
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