When Isaiah O’Brien walks out at Wellington Oval on Thursday, he will become the third member of his family to play for St George’s.

O’Brien is following in the footsteps of Samuel Paynter, his great-grandfather, and uncle George O’Brien, who both represented the East End club.

Paynter, the oldest living Cup Match player at 96, played in the Annual Classic from 1949 to 1956, with a best score of 81 runs. George O’Brien, who is now part of the St George’s coaching staff, did duty between 2005 and 2022, with his finest figures being eight for 76, picked up at Somerset Cricket Club in 2014.

Isaiah O’Brien is following in some illustrious footprints and is hopeful of making his mark

“It’s exciting to play in Cup Match after my great-grandfather and my uncle,” the 17-year-old told The Royal Gazette.

“My great-grandfather is the oldest living Cup Match player. He played for St George’s and to play in him and my uncle’s honour is a huge privilege.

“I wasn't born when they started playing Cup Match, but at least I got to witness my uncle play.”

O’Brien is expected to play a huge part across the two days with his all-round prowess likely to keep him constantly involved.

“I believe I’ll be playing as a shift bowler to come on and try to get a wicket,” he said.

“It’s all about bowling Somerset out twice. To be able to bowl and take wickets will be key for us wrestling it back from them. We've to really bowl well, take wickets and that’s the only way we’ll be able to bring the cup to the East.

“I’m developing into a batting all-rounder, scoring runs and being able to bowl when I’m needed.”

O’Brien, a member of the Bermuda Under-19 squad heading off to Atlanta, Georgia, for the ICC Under-19 World Cup Qualifier Americas Region next week, made the St George’s team having not featured as a reserve. He played in Colts Cup Match three times and bowed out on Sunday without tasting defeat.

“I just used to be a water boy, but I was never a reserve for St George’s,” O’Brien said.

“I had the honour of representing St George’s in the Colts Cup and I finished my career unbeaten.”