Simmons' first home was in Arima, Trinidad, a few miles outside Port of Spain. He lived just two doors down from Larry Gomes, a former West Indian batsman. 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.

He played cricket for a number of first-class sides in the West Indies and England as well as international cricket for the West Indian cricket team. He was voted a Wisden Cricketer of the Year in 1997.

In his career in first-class cricket, he averaged 35.61 with the bat and 28.68 with the ball. During the 1996 season with Leicestershire, he accumulated 1244 runs and took 56 wickets and 35 catches, helping his side to win the County Championship that year for only the second time in their history.

However, like many cricketers before him, he found the transition to Test level difficult, although he proved more adept to at the international one day game by scoring 2 half centuries in w.c. 1987 at beginning of his O.D.I career ( 50 runs off 57 balls at his debut match vs Pakistan & 89 runs off 126 balls vs Sri Lanka. In W.C. 1992, Simmons got 4 matches to play (v Zimbabwe, he scored 21 runs off 45 balls, v India, he scored 20 runs off 22 balls, v Sri Lanka, he scored 110 runs off 125 balls and v Australia, he scored none). At Sharjah Champions Trophy in 1993, Simmons won the player of the series award by scoring 3 half centuries for achieving 330 runs as batsman. In World Series Cup 1995/96, which included host Australia and Sri Lanka, Simmons failed to impress through his all rounder performances which cost his place for the world cricket cup which was held in Pakistan, India and Sri Lanka.

In December 1992, during the 8th match of the Benson & Hedges World Series tournament, Simmons won the Man of the Match award for his match-winning spell of 10 overs, 8 maidens, 3 runs, 4 wickets, with an economy of 0.30, against Pakistan. With this, Simmons holds the world record for most economical (conceding less runs) bowling in an ODI among those who completed their maximum quota of overs (10 overs in a 50-over match). In 1993's Sharjah Champions Trophy which included Pakistan and Sri Lanka, Simmons scored 3 half centuries, 2 of them against Sri Lanka, 92 runs off 161 balls and 90 runs off 109 balls and 1 against Pakistan (81 runs off 94 balls). Simmons won player of the series awards for achieving 330 runs as batsman.

During a 1988 tour match against Gloucestershire on his debut tour of England, he was struck on the head by a fast ball from David Lawrence in bad light at Bristol. His heart stopped and he required emergency surgery at Frenchay Hospital, from which he recovered fully.

Simmons retired from playing in 2002, then embarked on a successful coaching career. He was first appointed as the head coach to the Zimbabwe cricket team