In 1999–2000, for the first time in his United career, Van der Gouw played enough games to claim a Premier League medal; he made 23 appearances in all competitions during that season, of which 14 were in the Premier League. He started in 11 Premier League matches, and in 3 others he replaced the faltering Mark Bosnich as a substitute. This run of relatively regular play included United's defeat in the 1999 UEFA Super Cup, and he also featured in some of United's Champions League matches, including a notable performance against group rivals Sturm Graz – in which he made a string of saves, kept a clean sheet and stopped a penalty from Ivica Vastić. He also made his only appearance in a FIFA-organised tournament, against South Melbourne in the 2000 Club World Championship.