Nicknamed "Woosie", Woosnam was one of the "Big Five" generation of European golfers, all born within 12 months of one another, all of whom have won majors, and made Europe competitive in the Ryder Cup.

Woosnam spent his early years on Tour driving around the continent in a camper van, living on a diet of baked beans to save money.

In 1987, Woosnam was criticised by anti-apartheid campaigners for playing a tournament in Sun City in apartheid South Africa, in contravention of the United Nations cultural moratorium.

[7][8] After winning the Torras Monte Carlo Golf Open in 1991, Woosnam had a decline in form in the second half of the year and said that he was suffering from exhaustion after playing in too many tournaments across the world.

In the late 1990s, his form began to fade, but he nearly made a spectacular comeback at The Open Championship in 2001, when he finished third despite suffering a two-stroke penalty for starting the final round with 15 clubs in his bag instead of the allowable maximum of 14.

While his caddie, Miles Byrne, was responsible for this error, Woosnam decided at the time not to dismiss him stating: "It is the biggest mistake he will make in his life.

[11] Later in 2001, at the age of 43, Woosnam became the oldest player to win the World Match Play Championship (not an official European Tour event at the time) when he beat Pádraig Harrington 2 & 1 in the final.

On 1 June 2008, Woosnam won his first stroke play title in 11 years at the Parkridge Polish Seniors Championship at Kraków Valley Golf and Country Club, finishing with a course record 63.