Andrea Pellegrino claimed an upset win over Frances Tiafoe at the Italian Open (Image: Clive Brunskill, Getty Images)
Italian qualifier Andrea Pellegrino has pulled off one of the most stunning upsets of the Italian Open so far, eliminating 20th seed Frances Tiafoe 7-6(8), 6-1 to advance to the fourth round. The world No. 155 came through qualifying to make his main-draw debut at the Masters 1000 level, and has now stormed into the last 16.
Pellegrino has more than doubled his prize money earnings for 2026 in one fell swoop. Heading into the tournament, he had accumulated $98,632. He is now guaranteed a €92,470 (around $108,000) payout for reaching the fourth round in Rome after beating Tiafoe.
The 29-year-old tennis player is also expected to climb back into the world’s top 130, edging closer to his career-high ranking of No. 125. Pellegrino defeated fellow Italian Luca Nardi on his Masters 1000 main draw debut, before facing 15th seed and reigning Barcelona Open champion Arthur Fils in the second round. It came as Serena Williams rushed Kevin Hart off the Netflix roast podium after her sister Venus delivered a gift.
However, Fils was forced to retire while trailing Pellegrino 0-4 in the opening set, later revealing he felt something in his hip and was unwilling to risk further injury with the French Open on the horizon. That allowed the world No. 155 to advance to the third round — and he has seized the opportunity with both hands.
Pellegrino came out firing, breaking Tiafoe twice to surge into a 4-0 lead, but the American mounted a fierce comeback. The qualifier was unable to convert two set points when Tiafoe served at 3-5, forcing a tiebreak. Set points were exchanged between both competitors, but ultimately the home favorite clinched the tiebreak 10-8.
Pellegrino doubled his career earnings after reaching the last 16 (Image: Clive Brunskill, Getty Images)
He rode that wave of momentum directly into the second set, dropping just one additional game while securing two more breaks to advance into the round of 16.
The 29-year-old collapsed to the ground in disbelief before Tiafoe made his way over to embrace Pellegrino and acknowledge his victory. This ranks as the second-biggest win of Pellegrino’s career – he defeated then-No. 19 Felix Auger-Aliassime at a Challenger last summer – but is undoubtedly among the most emotional.
“It’s amazing. I didn’t expect, when I came here, at the beginning of the tournament, I didn’t expect to reach these kinds of rounds, but I’m very happy about my game. I played five matches and really good level, so I’m so happy,” Pellegrino said immediately after reaching the fourth round on his Masters debut.
“I mean, I come from a tough period, I got injured on my back last month, I didn’t play a few tournaments. I missed Monte Carlo, these tournaments, and to be here in Rome, it’s really special for me and reach fourth round in main draw, it’s something special.
“I started very well. At the beginning, I was playing very good. He wasn’t, I think, but then I started to think about… I was up and I became a bit tight, and his level goes up, and the match was not easy because of the wind, also. The conditions were not easy, but I was there every point, fighting every point, and I’m very happy about that.”
Pellegrino could now find himself competing in the most significant match of his career, as he awaits the outcome of a showdown between world No. 1 Jannik Sinner and Alexei Popyrin. Should compatriot Sinner advance, it would not be their first encounter on court. The four-time Major champion defeated Pellegrino 6-1 6-1 in a Futures final back in 2019.
“Yeah, yeah, of course I remember that. I think I won two or three games in the final!” the qualifier grinned. “He has to play, I think, no? So if I’m going to play with him, it’s going to be, of course, a really good match, good experience for me. Maybe we play on Centre, where I never played, but I’m very happy.”