That same month, before playing Nicolás Massú of Chile in the first match of the tie, Sela said: "We like being the underdog. I'm very pleased with the fact that I'm playing first and I'm very confident of claiming the win." He then proceeded to upset Massu, ranked #72 in the world, and formerly ranked #9 in the world, in a 5-hour 7-minute match. "This is definitely the biggest win in my career", Sela said afterwards. Later in that Davis Cup tie, Dudi Sela defeated #7 in the world Fernando González in a 5-hour 1-minute match. It is arguably the greatest tennis match ever played in Israel. The victory lifted Israel over Chile and into 2008's World Group. Gonzalez was at the time the highest-ranked player Sela had ever beaten in his career (he later beat world #5 David Ferrer in Beijing in September 2008), and his 6th upset of a top-100 player in the first 9 months of the year. Elated, Sela said "This is definitely the happiest day of my life." Sela was congratulated over the phone by Prime Minister Ehud Olmert and President Shimon Peres after the match.