In 2016, Tsitsipas had a breakout year, reaching at least the quarterfinals of all eight tournaments that he played, including all four Grand Slams.[1] He became the top-ranked junior in the world after winning his first Grade A title at the Trofeo Bonfiglio.[18] Tsitsipas also won the European Junior Championships later in the year.[19] Tsitsipas's biggest title of the season came in doubles, when he partnered with Estonian player Kenneth Raisma to win his only junior Grand Slam event at Wimbledon.[20] He became the first male Greek to win a junior Grand Slam in the Open Era, and the second overall after Nicky Kalogeropoulos won both the French Open and Wimbledon in 1963.[5] Besides his doubles triumph, Tsitsipas also had his two best finishes in the Grand Slam singles events that year, making the semifinals of both Wimbledon and the US Open.[21][22] He ended the year as the No. 2 ranked junior in the world, behind only Kecmanović who had played several more events.[23]