Roger Federer was unceremoniously dumped out of the Shanghai Rolex Masters in the second round by Albert Ramos-Vinolas on Tuesday.
The world number 70 edged the 17-time grand slam winner 7-6(4), 2-6, 6-3 on the hard courts of Shanghai in China.
The duo traded service games in the opening set with Ramos-Vinolas fighting off two break points. The Spaniard then raced to a 5-2 lead in the tiebreak.
But the second seed would find good rhythm in the second set, winning the final four games in a row to set up a decider.
One break of serve was all Ramos-Vinolas needed in the tense final game to sneak his first win over the former world number one.
Ramos-Vinolas advances to the third round where he faces 16th seed Jo-Wilfried Tsonga, who defeated Victor Estrella 6-3, 6-2 later in the day.
Ninth seed Milos Raonic lost just one service game in his 7-6(5), 7-6(2) win over Thomaz Bellucci, which books him a place in the second round with Roberto Bautista. 12th seed Kevin Anderson made short work of Tommy Haas, easing past the German 6-3, 7-5.
In the final game of the day, former US Open winner Marin Cilic eased past Borna Coric 6-1 6-2 in just 61 minutes.