Stuart O'Keefe

Youth

Having attracted the attention of scouts from several clubs whilst playing for local youth team Scole Lads, O'Keefe was invited to train with Norwich City's under-nine team. However, he later signed a youth deal with their East Anglian rivals Ipswich Town, joining the club at the age of nine and playing alongside Jordan Rhodes and Ed Upson in the academy during his time at the club. However, he failed to make an appearance for the first team and was released at the end of the 2006–07 season after Ipswich decided against offering him a scholarship, believing that he would be unable to compete physically at under-18 level. O'Keefe later commented on his release "It was disappointing to be released by Ipswich, especially since I had been there from such a young age, but I always kept believing in myself". Following his release, O'Keefe spent one month on trial at Aston Villa and impressed the club's coaching staff, including youth coach Gordon Cowans, but was forced to leave the club, who were only willing to offer him a one-year youth contract, after struggling to travel to the Midlands-based club on a regular basis as he continued to prepare for his GCSEs. He was also offered a trial with Nottingham Forest, scoring during a friendly match for the club but O'Keefe again moved on after Forest stalled over offering him a contract as they were only willing to offer him a one-year youth deal.

Southend United

O'Keefe attended a trial with Southend United in…

After originally beginning his career as a winger, O'Keefe switched to central midfield and was described by former Cardiff City manager Russell Slade as a "hard working, energetic, athletic midfield player." Slade also praised O'Keefe for his determination when not playing regularly in the first team, stating " Stuart will roll his sleeves up, work harder, to try and show his manager and the coaching staff that he's capable of playing in the first team."

As of end of 2023–24 season

O'Keefe was born in Eye, Suffolk. He grew up in the village of Gislingham, Suffolk and attended Gislingham Primary School and later Hartismere School. He is a supporter of Arsenal.