3 Tennis players with a cumulative winning head-to-head record against Federer and Djokovic

#3 Filippo Volandri (2 wins / 3 matches, 67%)

Filippo Volandri

Among all the illustrious players to have beaten both Federer and Djokovic, Filippo Volandri is perhaps the most surprising name.

The Italian has played Federer both times at his home tournament in Rome. He lost to the Swiss maestro in the 2003 quarterfinals in straight sets, before beating the dominant World No. 1 in three sets in the second round of the same tournament four years later.

Volandri's only meeting with Djokovic came in the opening round at 2004 Umag, where he beat the young Serb in straight sets. In his second ATP singles match, the then 368-ranked Djokovic endured the first defeat of his professional career en route to ending his debut year on tour with a 2-3 win-loss record.

The Italian is in a rarefied group of 8 players, 4 of whom are still active, who have never lost to Djokovic. For over one and a half decades, Volandri remained the only Italian player to beat Djokovic - until Marco Cecchinato beat the Serb in the 2018 French Open quarterfinals.

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