Andrey Rublev's Nitto ATP Finals hopes were dented after suffering a first-round exit against Francisco Cerundolo at the Paris Masters.
Rublev, who currently occupies eighth place in the Race to Turin, cut a frustrated figure as he was beaten 7-6 (8-6) 7-6 (7-5) by his Argentine opponent.
A semi-finalist at the indoor ATP Masters event 12 months ago, the sixth seed broke early for a commanding 5-2 lead in the opening set.
However, Cerundolo came roaring back, breaking twice for a 6-5 advantage, before drawing first blood in the tie-break.
Once again, Rublev was in control of the second set, with his second break putting him 4-2 to the good.
But Cerundolo hit back once more, breaking in game eight and then prevailing again in the tie-break for the 100th ATP win of his career.
His reward is a showdown with Stefanos Tsitsipas, who beat Alejandro Tabilo 6-3 6-4.
Data Debrief: Rublev's ATP Finals fate in the air
It took two hours and 18 minutes, but it was worth the wait for Cerundolo, who won his fourth match in seven against a top-10 opponent in 2024.
The Argentine struck 35 winners, while winning 86% (six out of seven) of points at the net.
As for Rublev, whose frustration culminated in him lashing the racquet against his knee, he must now nervously await his ATP Finals fate.
Tsitsipas, Alex de Minaur and Grigor Dimitrov are among the players in action this week who could deny the Madrid Open champion his fifth successive appearance at the year-end championship.
Griekspoor heroics send the Netherlands to historic Davis Cup final
Tallon Griekspoor produced a thrilling comeback to help the Netherlands reach the Davis Cup final for the very first time after they downed Germany 2-0 in Malaga.
After losing the opening set to Jan-Lennard Struff, Griekspoor held his nerve to emerge a 4-6 (4-7) 7-5 6-4 victor on an enthralling day of action on Friday.
Earlier in the day, Botic van de Zandschulp, who beat Rafael Nadal in the final match of the Spaniard's career on Tuesday, put the Dutch 1-0 up with a win over Daniel Altmaier.
The world number 80 needed 10 match points to wrap up a tense 6-4 6-7 (12-14) 6-3 victory, after Altmaier saved five break points in a second set tie-break.
Griekspoor then stopped the best-of-three tie from going to the deciding doubles, rallying back with a fine display, though Struff let two crucial break points slip in the eighth game of the second set.
“We have been talking about this [moment] for two or three years,” said Griekspoor.
“We came here all the time with unbelievably tough draws, but we believed in ourselves so much. We always felt like this was possible.
"To do it now feels unbelievable. I am so happy for the team, and for Holland.
“I just tried to focus on my own game. I felt like he was playing unbelievable tennis, I didn’t do much wrong in the first set.
"I’m super proud of myself, super proud of the effort and very happy to get the win in the end.”
The Netherlands await either reigning Davis Cup champions Italy or Australia, who face off in the other semi-final on Saturday.
Data Debrief: Dutch delight
After reaching the semi-final stage for only the second time this century, the Netherlands produced arguably their finest display of the tournament against Germany.
It meant that after 185 ties played at the event across a 104-year timeframe, they had finally reached the showpiece match at the tournament for the first time.
But their victory was made possible by Griekspoor, who converted both his break points, while fittingly sealing his encounter with his 25th ace of the contest.
France 37-23 Argentina: Les Bleus wrap up campaign with third win
France posted a comfortable 37-23 win over Argentina on Friday to make it three wins out of three tests at the Stade de France to conclude their Autumn Nations Series.
Having also beaten New Zealand and Japan in Paris this month, Fabien Galthie's side claimed four tries, including a superb solo effort from Louis Bielle-Biarrey, as they eased to victory against the Pumas.
The hosts led 30-9 at the break after Argentina's Julian Montoya and Juan Martin Gonzalez were both shown yellow cards in the first half, with Thomas Ramos slotting his third penalty of the game.
Tomas Albornoz made it 30-16 for Felipe Contepomi's visitors, but their hopes of a comeback were dashed as Bielle-Biarrey scored his fourth try in three games before Ramos made it 37-16.
Albornoz then cut the deficit to 37-23 with a two-pointer with nine minutes to play, but that wasn't enough to stop his side from falling to a defeat.
"We knew it was going to be an 80-minute game. We saw last week how Argentina went all the way against a good Irish team," France lock Emmanuel Meafou told TNT Sports.
"We are happy with the win. We have three from three [in the autumn] and we will look to build on that in the Six Nations next year."
Plymouth Argyle 2-2 Watford: Two-goal Gray rescues point for Rooney's side
Andre Gray scored twice against his former club to salvage a point for struggling Plymouth Argyle as they drew 2-2 with Watford on Friday.
Gray curled in an equaliser in the sixth minute of second-half stoppage time to seal a crucial point for Wayne Rooney's side in their bid for survival in the Championship.
The visitors made a quick start at Home Park when Ivorian striker Vakoun Bayo bundled in a cross from Yasser Larouci only eight minutes in.
Plymouth did, however, equalise against the run of play in the 23rd minute when Lewis Gibson's long ball into the box was met with a spectacular volley from Gray.
Watford regained the lead before the break when Imran Louza's free-kick was knocked back by Mattie Pollock, with centre-back Ryan Porteous on hand to steer the ball home.
But just as it looked like Watford would go home with all three points, Gray picked up the ball on the edge of the area and fired home a stunning effort beyond Daniel Bachmann.
Tom Cleverley's Watford sit in fifth place and trail leaders Sunderland by five points, while Plymouth are 17th with 17 points from 16 matches.
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