Last time when the No.1 and No.2 seeded players in men’s singles did not advance into the QFs at any Grand Slam :
2004-Roland Garros: Federer (1.) lost vs. Gustavo Kuerten in R32; Roddick (2.) lost against Olivier Mutis in R64.
2002-Aussie Open: Hewitt (1.) lost vs. Alberto Martin in R128 (R128); and Kuerten (2.) also lost vs. Julian Boutter in R128
2000 – US Open: Andre Agassi (1.) lost vs. Arnaud Clement in R64; Gustavo Kuerten lost vs. Wayne Arthurs in R128.
1967 – Wimbledon: Manuel Santana (1.) lost Charlie Pasarell in R128; Roy Emerson (2.) lost vs. Niki Pilic in R16.