Jacob Christopher Gleeson (born 26 June 1990) is a New Zealand footballer who last played as a goalkeeper for American club Portland Timbers.
Gleeson began his career playing for Western Suburbs FC of the Central Premier League. After an extremely impressive showing at the 2007 Under-17 World Cup in South Korea, Gleeson was offered week-long trials with English Premier League clubs Manchester United and Everton. During the trials, Gleeson impressed the management of both clubs but was suffering the effects of lingering illness, which management took into account. After the initial trial, Everton offered Gleeson a retrial which ultimately ended without an offer being made. Although Manchester United did not offer a retrial, they thought highly of Gleeson and goalkeeping coach Richard Harris promised to recommend Gleeson to other English clubs for a place in their academies.
Gleeson moved up to a higher division in 2008 by signing for Team Wellington of the ASB Championship, the national association football league of New Zealand, and spent the next two years with the club, featuring in 5 games in total.