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 November 2007 at the age of 16, having been recommended to the club by a scout working for Manchester United, and was offered a two-year scholarship just days after arriving at the club. In his first season with the academy, O'Keefe was part of the Southend team that reached the quarter-final of the FA Youth Cup and also featured for the reserves on several occasions. O'Keefe made his first-team debut for Southend on 18 November 2008, at home to A.F.C. Telford United in a 2–0 win in the FA Cup first-round replay as a late substitute in place of Alan McCormack, having signed his first professional contract with the club the week before. He made his debut in League One two months later against Leyton Orient on 20 January 2009 in a 1–1 away draw, again coming on as a substitute in the 84th minute for Alex Revell and nearly scoring late in the match with a volley. The following week, after one further substitute appearance, O'Keefe was handed his first league start for Southend by manager Steve Tilson against Leeds United at Elland Road on 27 January 2009. However, this proved to be his last appearance for the club during the 2008–09 season. Despite this, O'Keefe was nominated for the League One Apprentice of the Year award, eventually losing out to Carlisle United defender Tom Aldred. The following season, O'Keefe featured more regularly for the first team, making nine appearances in total despite missing two months of the season due to a hernia injury sustained in a match against Millwall on 26 January 2010. Following his departure from Roots Hall, the club's head of youth director Ricky Duncan praised O'Keefe's attitude, stating "Stuart was always very driven and single-minded and he was different to a lot of the other lads in that regard." Crystal Palace On 18 August 2010, O'Keefe signed for Crystal Palace on an initial one-year contract after impressing manager George Burley in a trial match against West Ham United reserves, having been recommended to Burley by his assistant manager Dougie Freedman who had played alongside O'Keefe at Southend. On his signing, Burley described O'Keefe as "a young