On 18 March 2007, Woolmer died suddenly in Jamaica, just a few hours after the Pakistan team's unexpected elimination at the hands of Ireland in the 2007 Cricket World Cup. Shortly afterwards, Jamaican police announced that they were opening a murder investigation into Woolmer's death. However, three months later they later announced that Woolmer had died of natural causes. The inquest into his death returned an open verdict.
Woolmer's first job was as a sales representative for ICI and his first senior cricket was with the Tunbridge Wells club and with Kent's second XI. In 1967 he broke the Kentish Leagues' Bat and Trap record for most consecutive strikes between the white posts - 13 in one game. Then in 1968, at the age of 20, he joined the Kent cricket staff and made his championship debut against Essex. His ability to move the ball about at medium-pace was ideally suited to one-day cricket at which he became a specialist. He won his county cap in 1969. Woolmer began his coaching career in South Africa in 1970-71 at the age of 22 and by 1975, when he made his Test debut, he had become a teacher of physical education at a prep school in Kent as well as running his own cricket school - at the time one of the youngest cricket school owners anywhere.
Woolmer was also a regular in England ODI cricket from 1972 to 1976. But Woolmer's international career stalled after he joined the World Series break-away group run by Kerry Packer. Though he appeared intermittently in the Test team up to 1981, he never recaptured the form of the mid 1970s. He also took part in the South African rebel tours of 1982, a move that effectively ended his international career..
Woolmer is thought to be the only man to witness both Brian Lara's innings of 501 not out vs Durham (1994) and Hanif Mohammed's 499 in Karachi in (1958).
Woolmer was known for his progressive coaching techniques. He is credited with making the reverse sweep a more popular shot for batsmen in the 1990s, as well as being one of the first to use computer analysis, and trying to adapt the knowledge of goalkeepers to wicketkeepers in cricket. He later attracted attention at the 1999 World Cup by communicating with his captain Hansie Cronje with an earpiece during matches. The practice was later banned.
He was appointed coach of South Africa in 1994. Initially his team performed poorly, losing all six matches on his first outing in Pakistan. However, in the next five years, South Africa won most of their test (10 out of 15 series) and One Day International matches (73%). However, the side failed to win either the 1996 World Cup or the 1999 World Cup, despite having the highest ODI success rate among international teams in that period.
At the 1996 tournament on the Indian subcontinent, his team won all their preliminary group matches before succumbing to the West Indies in the quarter finals.
At the 1999 tournament, South Africa faced Australia in the final match of the Super Six round; Australia needed to win to qualify for the semifinals, whereas South Africa had already done so. Australia boasted a superior recent record in must-win matches against South Africa. Media speculation was focused on Woolmer's team being less adept at handling high pressure situations. In the 1997/98 Australian international season, they had lost all four of their qualifying matches in a triangular tournament and conceded a 1-0 finals series lead, before recovering to take the series 2-1. The Super Six match saw Australia win the match in the last over, after Herschelle Gibbs dropped Australian captain Steve Waugh in a premature celebration of a catch. Waugh went on to score an unbeaten century and score the winning runs. The semifinal rematch saw a late Australian comeback culminate in a tie, when with match scores level, South African batsmen Lance Klusener and Allan Donald had a mix up, with Donald dropping his bat and being run out. As a result South Africa were eliminated due to their inferior performance in the earlier matches. and Woolmer resigned.
Woolmer was a strong candidate to replace David Lloyd as coach of England in 1999 but wanted a break from cricket and was reluctant to lead England in a tour of South Africa so soon after having relinquished the South Africa coach job.
He later returned to Warwickshire, and gained attention when he called for the removal of a life ban on South African captain Hansie Cronje for match-fixing. Woolmer spoke openly about Cronje and match fixing in an interview on the BBC TV programme "Panorama" in May 2001
He then worked for the International Cricket Council in helping with cricket development in countries where the sport was not well established.
He was appointed coach of the Pakistan team in 2004. This came after Javed Miandad was sacked when the Pakistanis conceded a 2-1 Test and 3-2 ODI series loss on home soil to arch rivals India, their first series win there in two decades. He was feted when his team reversed the result in early 2005 on their return tour to India, drawing the Tests 1-1 and winning the ODI series 4-2. In 2005 Pakistan beat England in a home series immediately after England had beaten the Australian team in the England to secure the Ashes. In the home series against India that followed, Woolmer's side were victorious in the Test series, winning it 1-0; however, the side lost the ODI series that followed 4-1.
Woolmer stated in 2006 that he believed that ball-tampering should be allowed in cricket and that a modification to existing laws should be made.
On June 12 2007, Lucius Thomas, the commissioner of the Jamaica Constabulary Force, announced that the investigation had concluded that Bob Woolmer died of natural causes, and was not murdered as indicated by the earlier pathologist's report. Three independent pathologists' reports commissioned by the police had found that the initial conclusion of manual strangulation was incorrect, and toxicology tests found no evidence of poisoning. The findings of the pathologists, and of Scotland Yard detectives who had visited Jamaica to assist with the investigation, were reported in the weeks leading up to the announcement, which was widely expected by the time it was made. Reports suggested that Woolmer suffered from health problems including an enlarged heart and diabetes, which may have contributed to his death..
On November 6, coroner Patrick Murphy asked for further tests to be carried out on samples taken from Woolmer's body following discrepancies in the toxicology reports by forensic scientists from the Caribbean and the UK.
After hearing twenty-six days of evidence, the jury at the inquest returned an open verdict, refusing to rule out the controversial strangulation theory put foward by Dr. Seshaiah.