One of Bermuda’s top sportsmen, revered as Cup Match’s most successful wicketkeeper, prided himself as an old-school and stylish player who gave back to the community as a sports administrator in several roles.

Dennis Wainwright Sr set an example as “a sporting giant and a man of unrivalled character on an off the field”, David Burt said.

The Premier added that the footballer and cricketer’s “flair and zest for the game shone through his entire sporting career”.

“He was model of sportsmanship and lived a full, fit and incredible life.

“On behalf of the Government and people of Bermuda, I extend condolences to his wife, children and the entire family.”

St George’s Cricket Club also offered condolences, adding: “Mr Wainwright was one of our Cup Match stalwarts and former captain. We were fortunate enough to have celebrated him while he was still here to smell the flowers. He will truly be sorely missed.”

The executive of the Bermuda Cricket Board and member clubs also posted a tribute to Mr Wainwright.

It added: “His dedication to advancing the level of multiple sports programmes on and off the field will not be forgotten.”

Hailing from a cricketing family, Mr Wainwright mastered etiquette as well as spirit of the game. He set records behind the stumps for Flatts Victoria Recreation Club as well as St George’s.

He started playing Cup Match for St George’s in 1956 as a reserve and quickly became a legend for the East End. His last Cup Match was 1977, but he still holds the record for most dismissals.

More recently, Mr Wainwright spent many years judging the Safe Hands Award for the best fielder at Cup Match.

As a footballer, Mr Wainwright represented the island in 1967 at the Pan American Games in Winnipeg, Canada, where Bermuda won a silver medal, and over his career he played for Wellington Rovers, St George’s Colts and Young Men’s Social Club.

Double international: Mr Wainwright was the island’s first double international, representing Bermuda as a football player and cricketer at the same time.

Owen Darrell, the sports minister, noted he served as “a wicketkeeper in Bermuda’s first-class cricket debut against New Zealand in 1972 and as a goalkeeper for the national football team”.

He was a longstanding member of the Bermuda Cricket Board as well as St George’s.

Mr Wainwright was introduced to bodybuilding by his older brother, Gilbert.

He became a keen proponent in later years, when he was a founder of the Bermuda Bodybuilding Federation, also serving as its president.

He was a vice-president of the International Federation of Caribbean and Atlantic Bodybuilders — also achieving a brown belt in jujitsu.

In 2005, he was appointed a Member of the Most Excellent Order of the British Empire for his service to sport and community, and in 2006 he was inducted to the Bermuda Sports Hall of Fame.

The sports legend also greatly enjoyed hospitality, working for the Bermudiana Hotel in Hamilton, where he started out as a nightclub waiter in 1958 and finished as the assistant manager in 1987.

“I loved it,” he told The Royal Gazette in a 2019 interview. “If I was to go to work again, I would like to work in hospitality. I love people.”

He and his wife, Natalie, celebrated their 60th anniversary that same year. The couple had three children: Dennis Jr, Deborah and Paula.

They attended Bethel African Methodist Episcopal, Hamilton Parish, Church, where Mr Wainwright was a trustee and served on its stewards and finance boards as well as singing in the choir.

Mr Wainwright made a name for himself for keeping his sports gear immaculate and dressing well off the field, with tailor-made shirts.

He told the Gazette: “Some people talk more about my attire than my actual playing.”

Mr Wainwright was born in Wellington, St George’s, but moved to Bailey’s Bay and then Flatts Hill in Smith’s in his childhood, attending Harrington Sound Primary School.

His father, Wilton, was a carpenter and his mother, Adrie, a homemaker.

Cricket dominated the neighbourhood world of his childhood.

He recalled: “Anywhere you found a flat backyard, there was cricket being played with either a real bat, or a piece of wood and a tennis ball.”

Mr Wainwright counted his uncle Philip “Busty” Wainwright as an inspiration. Both his father and uncle played county cricket for Flatts.

In a tribute online, Mr Darrell hailed Mr Wainwright as “a true Bermudian legend and my cherished neighbour”.

He added: “His contributions to sport and the community will never be forgotten.”

Mr Darrell said his legacy would “continue to motivate and inspire generations to come”.

Former MP Rolfe Commissiong, whose Black Star Communications presents the annual Cup Match Safe Hands Award, said Mr Wainwright was its head judge from its inauguration.

Mr Commissiong added: “He was with it right up until 2024, its 25th anniversary. When he headed the bodybuilding federation, he invited me to be a judge for several years.”

He said Mr Wainwright was widely known by “his status on the legendary Cup Match squad led by Calvin ‘Bummy’ Symonds — the greatest squad in Bermuda history”, adding that he and Lee Raynor stood out as “the smartest, sharpest-looking guys in Cup Match”.

“He is going to be very sorely missed.”

• Dennis Arlen Wainwright Sr, inducted into the Bermuda Sports Hall of Fame in 2006 as a cricket and football icon, was born on November 17, 1935. He died in December 2024, aged 89