[citation needed] His career progressed slowly and at a low profile for many years as fellow British boxers were reluctant to face him.

In September 2000 he won the Commonwealth Middleweight title by outpointing Australian-based Egyptian (and future #1 contender) Sam Soliman, and finally began receiving wider coverage.

[1] Following this match, U.S. promoter Don King signed him up and in November 2001 he fought two-time champ William Joppy for the vacant WBA world title on a Lennox Lewis undercard in Las Vegas.

He defended the European title twice more, stopping ex-world champion Hacine Cherifi in eight rounds in July 2003 and outpointing Sergey Tatevoysan in January 2004.

Now with a 40-1 record and highly ranked by all sanctioning bodies, Eastman finally got the forty-year-old undisputed Middleweight king Bernard Hopkins into the ring to defend his titles, in February 2005 in Los Angeles.

In April 2007, Eastman added the Commonwealth belt to the British title with a 12-round points decision over the Kenyan Evans Ashira in Dudley.

When defending his British title against domestic fighter Wayne Elcock Eastman was surprisingly outworked and outpunched, dropping a shock points defeat by margins of 113-116, 113-115, 114-115.

He beat Denny Dalton to claim the Guyanese middleweight title, before securing victories over former WBA world welterweight champion Andrew Lewis, Leon Gilkes and Kevin Placide.