Complex sentence: He was the captain of the Singapore national team in the late-1990s and early-2000s, and led the team which won the regional Tiger Cup (later renamed the ASEAN Football Championship) in 1998.
Split into simpler sentences: He was the captain of the Singapore national team in the late-1990s and early-2000s. He also captained the Singapore team which won the regional Tiger Cup (later renamed the ASEAN Football Championship) in 1998.