He got started in the game at age 11 by his mother, who thought a nearby nine-hole course would be a great babysitter for him and his brother David.

[1] The biggest win of his career was his first on the Champions Tour, and came in a major – The 2004 Senior British Open played at Royal Portrush Golf Club in Northern Ireland.

[2][3] Oakley sank a 10-foot par putt on the final hole to win by one stroke and avoid a playoff with Tom Kite and Eduardo Romero.

The victory made him only the 10th open qualifier to win a Champions Tour event.

In 2001, he completed and opened (with partner Chris Adkins) a public course in Milton, Delaware, called The Rookery Golf Club.