Webb had a long connection with England cricket sides appearing for Brighton and Hove CC, Elland Cricket Club, Dulwich Cricket club and Stafford Cricket Club. Webb also made one appearance for Staffordshire Minor County Side. He appeared as Professional for Elland, and Stafford Cricket Clubs, winning the Sykes Cup in 1979 with Elland cricket Club. Webb was the first of many Young Auckland Cricketers, to benefit from the Support of the Auckland Cricket Society which enabled him and many others to travel to England and improve their skills. Many others followed from Webb's first example. Shortly later the New Zealand Cricket Council started the Lords Cricket Scholarship with Martin Crowe the first recipient. Webb also spent considerable time with Coaching Janette Brittin, English Womans Cricketer, living with her and her family in Chessington, Surrey. Janette Brittin was to finish her career as England best ever batsman in both Test and One Day cricket. In Auckland New Zealand, Webb played for initially Te Atatu Cricket Club as a youngster, scoring his first century for the Te Atatu 4th Grade men's side against University when aged 14 years of age, followed by Suburbs Cricket Club and Finally Cornwall Cricket Club. At each club Webb was prolific with his contribution not only on the field but also with Coaching and mentoring players including, Mark Greatbatch and Adam Parore who both went on to successful careers with New Zealand Cricket. For Auckland, Webb played for Auckland Primary Schools 1967/68, Webb was also selected as Captain of the North island primary schools side, then Brabin Shield Cricket at 16 years of age, Rothmans Under 23 at 17 years of age and Auckland at 18 years of age. He Captained Auckland at each of these levels. He Captained Auckland to a one-day Shell series Championship. He also achieved selection for New Zealand Brabin and Rothmans sides, Young New Zealand and full New Zealand Selection. Webb also played one game for Staffordshire in England. Webb was first selected to appear for Auckland replacing Ross Morgan, as an opening batsman and as his career developed he was a successful middle order batsman as well as also keeping wicket in both one day and first class cricket for Auckland. Both Webb and John Reid benefited from these early years of input from Graham Vivian and Mark Burgess. Webb was in 2 successful First Class Championships and in 2 One Day Shell Series wins, Captaining one of the One Day Shell Series. In 1986 Webb attended Marlborough College in Wiltshire as part of a Scholarship to study Sports Turf Maintenance and was under the supervision of Peter Mansfield NDT, Webb attained the Institute of Groundsman NTC and NPC in 1986, Webb was the first overseas candidate to sit and pass these qualifications. Webb went on to be Head Groundsman at Reading Blue Coat School and at Reeds School in Surrey. At both these schools Webb also Coached Cricket. In New Zealand Webb worked at Eden Park Auckland as a Groundstaff member, and later at Melville Park in Auckland where he was Head Groundsman. It was at Melville Park that Webb received a merit commendation for his skill and Training schedules he was instrumental with.