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Legends XI
In the summer of 2008, Growsport ,a local sports promotion company announced that they would be hosting a Legends tournament at the Oval, consisting of Legends teams from Glentoran, Linfield, Manchester United and Liverpool. The Glentoran Legends XI was entrusted into the hands of Billy Caskey, who in turn enlisted the help of Philip Stevenson to bring together a squad of ex-Glentoran players to represent the club in what would be known as the Umbro Cup. The squad on that July day consisted of many illustrious names from Glentoran's recent history such as Jim Cleary, Johnny Jameson, Barney Bowers, Liam Coyle, Gary Blackledge, Chris Walker and Gary Smyth. Sadly, they lost their opening match to Liverpool and in turn lost in the third/fourth place play-off to Linfield but it sowed the seeds for a Glentoran Legends XI to come together to play on a regular basis.
For the Umbro Cup, Growsport had organised sponsorship for each team, with the Hilton Hotel sponsoring Liverpool , Mascott Contruction sponsoring Manchester United and the Belfast Telegraph sponsoring the shirts of both Linfield and the Glentoran Legends XI's.
With the momentum gained from playing together again, the Legends have continued to come together on a regular basis since the summer and thanks to the support of the 1923 Glentoran Supporters Committee, they had a new Umbro kit designed , with the Glentoran Gazette as the shirt sponsor and a new dedicated badge was added. In May and June of 2009, the Legends will be playing in three very special matches, firstly against a Glentoran Community Trust Supporters XI, then they will face a Crusaders Legends XI at Seaview before travelling up to the Brandywell to face a Derry City Legends XI.