Damiano Caruso became the first rider to claim a mountain stage on two different Grand Tours this year as he won stage nine of the Vuelta a Espana.
The Bahrain-Victorious rider, who came second at the Giro d’Italia in May, produced a superb solo ride as he crossed the line in five hours, three minutes and 14 seconds.
Defending champion Primoz Roglic came second to increase his overall lead.
Enric Mas, who finished third, is now 28 seconds behind the Slovenian.
Caruso spent the final 70km of the 188km stage from Puerto Lumbreras to Alto de Velefique out in front, and while he faced pressure from Roglic and Mas towards the end, the 33-year-old held firm to take his second individual Grand Tour stage victory, having also claimed stage 20 of this year’s Giro d’Italia.
Mas launched a spirited attack in the final four kilometres but Roglic out-sprinted him to beat the Spaniard by a second.
With the six seconds he earned for finishing second, compared to the four awarded to Mas, he extended his lead over the Spaniard by three seconds.
Miguel Angel Lopez is one minute and 21 seconds behind Roglic in third, with Jack Haig one minute and 42 seconds back in fourth.
Giro champion Egan Bernal is one minute and 52 seconds behind in fifth while Great Britain’s Adam Yates moves into sixth, two minutes and seven seconds off Roglic.
Stage nine results
1. Damiano Caruso (Ita/Bahrain Victorious) 5hrs 3mins 14 secs
2. Primoz Roglic (Slo/Jumbo-Visma) +1min 05secs
3. Enric Mas (Spa/Movistar) +1min 06secs
4. Jack Haig (Aus/Bahrain Victorious) +1min 44secs
5. Miguel Angel Lopez (Col/Movistar) same time
6. Adam Yates (GB/Ineos Grenadiers)
7. Gino Mader (Swi/Bahrain Victorious) +2min 7secs
8. Giulio Ciccone (Ita/Segafredo) +2min 10secs
9. Egan Bernal (Col/Ineos Grenadiers) same time
10. David de la Cruz (Spa/UAE Team Emirates) +2min 40secs
General classification standings after stage nine
1. Primoz Roglic (Slo/Jumbo – Visma) 34hrs 18mins 53secs
2. Enric Mas (Spa/Movistar) +28secs
3. Miguel Ángel Lopez (Col/Movistar) +1min 21secs
4. Jack Haig (Aus/Bahrain Victorious) +1min 42secs
5. Egan Bernal (Col/Ineos Grenadiers) +1min 52secs
6. Adam Yates (GB/Ineos Grenadiers) +2min 7secs
7. Giulio Ciccone (Ita/Segafredo) +2min 39secs
8. Sepp Kuss (US/Jumbo – Visma) +2min 40secs
9. Felix Grosschartner (Aut/Bora-Hansgrohe) +3min 25secs
10. David de la Cruz (Spa/UAE Team Emirates) +3min 55secs