He played international cricket for the West Indies from 1987 to 1999 as an opening batsman and right-arm medium pace bowler.
He proved to be adept at a number of sports, but excelled at cricket and was soon playing for the regional side East Zone.
He made the leap to represent Trinidad and Tobago in 1983 with the help and encouragement of Rohan Kanhai, the coach at East Zone.
[1][2] At the domestic level, Simmons featured for Trinidad and Tobago, English sides Durham and Leicestershire, along with South African clubs Border and Easterns.
He went on to accumulate 1,244 runs with 56 wickets and 35 catches, helping his side to win the County Championship for only the second time in their history.
With Simmons at the helm, Leicestershire went on a six-match winning streak and eventually claimed the title with a resounding triumph over Surrey at The Oval.
At the 1995–96 Australian Tri-Series which also included Sri Lanka, Simmons failed to impress for which he was not selected for the 1996 World Cup.
[8] He found himself having to defend Zimbabwe's Test status in the midst of a losing streak, which included losses to Bangladesh and New Zealand.
[3][9][10][11] Simmons then succeeded Adrian Birrell as coach of the Ireland national cricket team after the 2007 World Cup.
[3] In June 2019, he was named as the coach of the Brampton Wolves franchise team for the 2019 Global T20 Canada tournament.
The Pakistan Super League (PSL) franchise Karachi Kings appointed him as the team head coach in 2023.