#2. Over Roger Federer in R2 at 2015 Madrid Masters
Roger Federer and Nick Kyrgios played the best match of the Madrid Masters during their second round encounter with Kyrgios edging out Federer to script one of the upsets of the tournament. Kyrgios began the tournament by defeating qualifier Daniel Gimeno-Traver in the first round in straight sets to set up a second round encounter against top seed Roger Federer.The match turned out to be one of the finest matches of the year with every set of the match going to a tie-break. Federer took the first set by winning the tie-break 7-2 before Kyrgios bounced back in the match to win the exciting second set tie-break 7-5. Kyrgios produced the upset of the tournament by winning an even exciting third set tie-break 14-12 to progress into the third round. However, he lost to John Isner in three sets.