Bucknor played as a goalkeeper in Jamaican parish leagues in the 1960s. In 1964 he played in goal for Jamaica in a schoolboy international versus Brazil, which Jamaica drew 1–1.
Bucknor's first international cricket fixture was a One Day International between the West Indies and India at Antigua on 18 March 1989. His first Test match was at Sabina Park, Kingston, Jamaica, between 28 April and 3 May 1989, with the competing teams again being the West Indies and India. After umpiring in a few international matches, he was selected to umpire at the 1992 Cricket World Cup in Australia, and went on to stand in the final despite being quite inexperienced. Bucknor also stood in the next four World Cup finals in 1996, 1999, 2003 and 2007, with the 2007 World Cup taking place in his native West Indies. In 1994 the ICC introduced a policy whereby one of the umpires in each Test match would be independent of the competing nations, selected from the International Panel of Umpires. Bucknor was a member of this panel from its foundation until the ICC changed its policy on umpires again in 2002. Since then both umpires in Test matches, and one of the umpires in ODIs have been independent of the competing countries. The officials are now chosen from the Elite Panel of ICC Umpires, whom the ICC consider to be the world's best umpires. Bucknor maintained a place on the Elite Panel from its foundation until his retirement. In May 2006, he accused TV companies of doctoring their images to make umpires look bad and key players look good. He was one of five officials, responsible for the wrong decision in the 2007 World Cup final, resulting in play continuing in poor light. Consequently, all five officials were suspended from the Twenty20 World Championship in South Africa. Dave Richardson, the general manager of cricket at the ICC, has said Bucknor's umpiring accuracy was at 96% during 2005–06, above the average of 94.8% for the Elite Panel. In 2007, he was short-listed for the Umpire of the Year award, which was ultimately won by Simon Taufel. Things turned progressively worse in the following months, when he was removed by the ICC from officiating in the third Test between Australia and India in Perth after his several incorrect decisions contributed to India's defeat in the second Test in Sydney in January 2008 & he was replaced by Billy Bowden for the third Test match. Former umpire Dickie Bird suggested that Bucknor had "gone on too long", while Bucknor blamed Indian cricket board BCCI's financial power for his ouster. The ICC confirmed on 23 February 2009 that Bucknor had decided to retire from umpiring in March 2009. His final Test match was the 3rd Test between South Africa and Australia at Cape Town on 19–23 March, and his last One Day International match was the 4th ODI between his native West Indies and England at Barbados on 29 March, bringing his 20-year career as an official to an end.
Achievements as an umpire
Cricket World Cup
Bucknor has stood as an onfield umpire in five World Cup tournaments, during which he has officiated 44 matches including five finals.
Test match record
Bucknor held the record for the most Test matches umpired until December 2019, when Aleem Dar of Pakistan stood in his 129th Test match as an on-field umpire, surpassing his record of officiating in the most number of Test matches. He was the first umpire to have officiated in over 100 Test matches.
Awards
Bucknor has received the ICC's Bronze Bails Awards for umpiring in 100 ODIs, as well as the Golden Bails Award for umpiring 100 Test matches.
