Has any tennis player held all four mens Grand Slam singles titles simultaneously?
Yes. Don Budge won the grand slam in 1938 and Rod Laver in 1962 and 1969. So on each of these occasions they were the holder of all four grand slam singles titles simultaneously. But strangely enough, no men have held all four singles titles across different years. In the women’s game, Maureen Connolly (1953), Margaret Smith Court (1970) and Steffi Graf (1988) have won calendar grand slams. There have also been players who have won four consecutive grand slams or more across different years. These include Martina Navratilova (1983-1984 – six slams in a row), Steffi Graf (1993-94), and Serena Williams (2002-2003).