His form fell away gradually in the new millennium, partly due to marriage problems, and his ranking slumped to 82nd in the world, but he came back strongly in 2005, winning a record eighth European Tour Order of Merit and returning to the top ten in the World Rankings. Late in 2005 he became the first man to win 20 million Euros on the European Tour—topping the European Tour's all-time highest earners list. He won for the first time in nearly two years at the Smurfit Kappa European Open in July 2007. In 2008, Montgomerie slipped out of the top 100 players in the world ranking system. A runner-up finish at the 2008 French Open in June boosted him back up the rankings, but his good play was short-lived, and as a result Montgomerie failed to qualify for Nick Faldo's 2008 Ryder Cup team. In March 2009, Montgomerie played in his milestone 500th European Tour event at the Open de Andalucia where he made the cut, but was not in contention during the weekend. He remained the leader in career earnings on the European Tour until 2010, when he was surpassed by Ernie Els.