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Bizarrely, the new away shirt was worn for the first time at home, against Bulgarian side Litex Lovech in the European Champions League in 1999. Made from the same material as the home version this was another plain yet striking shirt. Worn with white shorts and socks it would get regular run outs during the two seasons it was retained as an away option. Again the shirt would be worn in 2000 when the side faced the Norwegians of Lillestrom in the UEFA Cup at the Oval and also against Glasgow Rangers as the Scottish giants finally fulfilled a long standing obligation to play Glentoran in a friendly at Ibrox as part of Tommy Leeman's transfer deal (which had been agreed 16 years previously).
Glentoran's progress through the early rounds of the Irish Cup was something of a white knuckle ride. The team looked to be heading for the exit door as early as the 6th round at Armagh, but for a Stuart Elliott equaliser late, late into stoppage time which salvaged a draw and a replay which the Glens would subsequently win. On the 8th April 2000 Glentoran were again drawn to face Linfield in the semi-final. With sponsorship still an issue, a plain shirt was provided for the clash at Windsor Park. With the ground packed to the rafters goals from Rory Hamill and Stuart Elliott looked to have sent the Glens into the final with a 2-1 victory. Late into injury time though, Murphy equalised for Linfield sending the home support into raptures. Whilst they celebrated though Glentoran centred and made one last gasp assault on the Kop end. The ball miraculously found its way into the penalty area and onto the head of Glens' new boy Sean Armstrong. Armstrong nodded the ball into the Linfield net causing scenes of almost mass hysteria inside half of Windsor Park. Glentoran were in yet another Irish Cup final.