Benkenstein was born in Salisbury, Rhodesia (now Harare, Zimbabwe), the son of Martin Benkenstein, who had played for Rhodesia in the Currie Cup in the 1970s. In 1980, around the time of Zimbabwean independence, Martin moved his family to Durban, South Africa. There, Benkenstein attended Durban Preparatory High School, Durban High School and Michaelhouse schools. He captained the SA Schools side in 1992, and led the SA Colts team to the West Indies in the same year.

Natal

Benkenstein made his debut at the age of 18 for Natal in the 1993/94 season, playing under the tutelage of Malcolm Marshall. Marshall's analytical captaincy style made an impression on the young Benkenstein, who was later quoted as saying "In my eyes, he took the art of captaincy to another level." When Marshall left Natal at the end of the 1996 season, Benkenstein, still only 22, was selected to succeed him as captain. While he got off to an unsteady start as captain, with Natal being heavily defeated by Border in his first game at the helm, he later recovered and led the team to win both the four-day and one-day domestic competitions.

Durham

When Benkenstein joined Durham for the 2005 season, he collected the club's player of the year award during his first attempt. During this time he also filled in as skipper for the absent Mike Hussey and Paul Collingwood. He went on to score 1,427 runs, which was a run scoring record at Durham until his mark was overtaken by Michael Di Venuto in 2009.

Dale has been quoted as to saying 2008 may be his last season in the sport as he wants to spend more time with his wife Jacqueline and children in Consett.

International career

Benkenstein had represented his country many times as a junior, including a stint as captain of the South African Schools side, and in the under-19 development team. Benkenstein's senior ODI debut for South Africa came against England at Dhaka in 1998/99, when the teams were playing in the quarter-final of the Wills International Cup. Despite some useful contributions, including 69 against the West Indies at Cape Town in 1998 and 3/5 against Kenya in the 2002/03 ICC Champions Trophy tournament, he never managed to establish himself as a permanent member of the team. Benkenstein later admitted that he had not taken full advantage of the opportunities that came his way at the international level.

He was named coach of Hampshire County Cricket Club in February 2014 as previously he work as a batting coach for the South African side Sunfoil Dolphins.^[6][7] He left his coaching role at Hampshire in July 2016 due to family reasons. ^[8]

Benkenstein was named one of the Wisden Cricketers of the Year in 2009, based on his work with Durham in the English county championship, despite being a failure and an unknown in the international arena due to the reversal in stance in 2004 with the introduction of a separate Wisden Leading Cricketer in the World award.^[1]