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. His international career didn't get off to the most auspicious start.
In March of 2015, The West Indies Cricket Board announced his appointment to the role of West Indies Head Coach on a three-year contract
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. He remains in close contact with the surgeon who saved his life, Nigel Rawlinson.
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 in 2004. This proved a difficult and controversial job, not least because he inherited a team heavily weakened thanks to the mass dismissal of most of the senior players.
He found himself having to defend the Test status of his country after an appalling losing streak, including a loss to Bangladesh who were widely seen as the worst Test side in the world. The Zimbabwe cricket union made him a scapegoat for the problems in the side and he was sacked under farcical conditions in August 2005 after persistent rumours of his impending dismissal. The official notice of his removal was dated two days before it was actually released. Many commentators felt that he was simply too kindly and naive to have succeeded in such a difficult position.
During that time, Ireland won 11 trophies, qualified for every major ICC event, and achieved victories over Pakistan and Bangladesh at the 2007 World Cup, England at the 2011 World Cup and the West Indies and Zimbabwe at the 2015 World Cup.
In March of 2015, he accepted an offer to coach to take charge of his native West Indies after the conclusion of the 2015 World Cup. WICB chief executive Michael Muirhead said of his signing, "Phil has a proven ability to develop players, while cultivating great team spirit and a winning culture, we have a number of young, talented players about whom he is excited to be coaching and we believe he is the right fit"
At the time the former top ranking cricket team was in a period of significant struggles, and he was tasked with bringing the team from near the bottom of the top ten rankings and back into prominence.
In Dec 1992, during the 8th match of "Benson & Hedges World Series" tournament, Simmons won the man-of-match award for his match winning spell of 10–8–3–4 (Overs-Maidens-RunsConceded-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 (10overs in a 50 over match).