Dick Advocaat

Dick Advocaat will, on June 14 in Houston, become the oldest manager ever to take charge of a World Cup match. At 78, he is older than the Netherlands national team’s first World Cup appearance — and he has been managing professionally for forty-two years. Nicknamed “The Little General” in tribute to his playing-days mentor Rinus Michels, Advocaat’s career is one of the most well-travelled in football history: PSV, Rangers, Zenit Saint Petersburg, Sunderland, Fenerbahçe, Feyenoord; the national teams of Netherlands (three separate spells), South Korea, Belgium, UAE, Russia, Serbia and Iraq.

The CV’s highlights are real: a 1994 World Cup quarter-final with the Netherlands, a 2008 UEFA Cup with Zenit Saint Petersburg (followed by the UEFA Super Cup against Manchester United), a Euro 2008 semi-final with Russia, and a domestic treble at Rangers in 1998-99 including a then-record £12 million signing of Tore André Flo. He has also had jobs go badly — short, unhappy spells at Borussia Mönchengladbach, Serbia, Sunderland, ADO Den Haag — but always lands the next one because his core skill is taking a defensively-disciplined organisation onto the pitch within weeks.

Curaçao is, by his own admission, a victory lap. Hired in January 2024, he treated the CONCACAF qualifying campaign like a club season: detailed pre-match preparation, almost no rotation, every player explicitly told their role. The team won Group B in the final round ahead of Jamaica, Trinidad and Tobago and Bermuda — including a 2-0 home win over Jamaica and an extraordinary 7-0 thrashing of Bermuda — and locked qualification in November 2025 with a 0-0 draw at Jamaica in the final fixture.

The Group E draw is brutal — Germany, Ecuador, Ivory Coast — but Advocaat has been here before. He spent his career setting up underdogs against larger nations and finding ways to make them awkward to play through. If Curaçao do manage a point at this tournament, it will be authored by a manager who has been planning exactly this kind of result since the 1980s.