The midfielder joined the Gunners as a trainee in 1983 and after making an impression over the following 12 months, he was offered contract terms by manager Don Howe.
Rocastle had problems with his eyesight during the early part of his career, but after he started to use contact lenses, his stint at Highbury took off. Alongside Michael Thomas and Paul Davis, Rocastle formed part of three-man midfield unit that would help to spearhead Arsenal to their success of the late 1980s and early 1990s.
He played a leading role in the Division One title-winning side of 1989, scoring six goals in the process. Rocastle was still at the club when they regained the trophy in 1991, but he was used much more sparingly.
A year later, much to his disappointment, the 1987 League Cup winner was sold to Leeds United for £2m. Speaking about that switch some time later, his former teammate Davis said: "He cried. We spoke about it quite often. He couldn't understand why they ever wanted him to go. The club's line was that he was injured, he was struggling with his weight, he'd had a knee operation. I don't think he ever recovered from the fact of leaving Arsenal, in his own mind."
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The move to Elland Road was a less than successful one, with injuries and competition for places limiting the number of appearances that he was able to make. That was followed by spells with Manchester City and Chelsea, as well as time on loan with Norwich City and Hull City.
Despite only being in his early 30s, Rocastle wound down his career with Malaysian side Sabah FA, before announcing his retirement in 1999.
It was just two years later and at the age of 33 that the former England international announced that he was suffering from non-Hodgkin's lymphoma, an aggressive form of cancer which attacks the immune system.
Affectionately known as 'Rocky' - particularly by those connected with Arsenal - he passed away 13 years ago today, survived by his wife Janet, son Ryan and daughters Melissa and Monique.
Paying tribute to Rocastle on the 10th anniversary of his passing, current Arsenal manager Arsene Wenger said: "He was a modern player, because the revolution of the game has gone to more technique and more skill. Rocastle not only had an exceptional dimension as a footballer, but as well a human dimension. Everybody liked him."