Winterburn held down a permanent spot in 'The Back Four' during the late 1980s and throughout the 1990s. His professionalism and appetite for the game commanded the respect of fans throughout his Highbury career. He was superbly accurate from the byline and had a cute knack of prising open defences with incisive back-to-front passes and supplied plenty of assists. One of his most memorable moments was his weaker right foot against former club Wimbledon in the closing stages of the 1988/89 Championship race. Winterburn's presence in the 'Double' side of 1998 was well merited and testament to his longevity. Winterburn joined West Ham United in June 2000 for a fee of £250,000.