Eight years after competing in his first Olympics, Michaelides qualified for his third Cypriot team, as a 29-year-old, at the 2000 Summer Olympics in Sydney. Swimming only in the 50 m freestyle, he posted a FINA B-standard entry time of 23.08 from the Akropolis Grand Prix in Athens. He challenged seven other swimmers in heat six, including Ukraine's rising favorite Oleksandr Volynets and Lithuania's Rolandas Gimbutis, the tallest swimmer at the Games. Michaelides toppled a new Cypriot record of 23.05 to pick up a third seed in his heat, finishing behind winner Volynets by almost half the body length. Michaelides failed to advance into the semifinals, as he placed twenty-seventh overall in the prelims.