Complex sentence: He was Arsenal's third-choice keeper, and did not play a single match in the 2005-06 season, although he became the first Estonian to receive a Champions League medal (albeit a runners-up medal) after Arsenal lost to FC Barcelona.
Split into simpler sentences: He was Arsenal's third-choice keeper, and did not play a single match in the 2005--06 season. However he became the first Estonian to receive a Champions League runners-up medal after Arsenal lost to FC Barcelona.