Frenchman Remi Cavagna sealed his first Grand Tour stage win on a day that featured mid-stage controversy in the Vuleta a Espana on Friday.
He launched a solo attack with just under 25km of stage 19 to go and held off his pursuers by five seconds.
Race leader Primoz Roglic was in a crash which split the peloton 65km out.
Alejandro Valverde’s Movistar team – against cycling convention – then attacked, but eventually slowed and Roglic was able to rejoin the peloton.
Movistar’s move angered many in the race, with fellow Spaniard Omar Fraile, who rides for Astana, remonstrating strongly with Valverde.
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Jumbo-Visma’s Roglic, who went into the day holding a lead of two minutes and 50 seconds, eventually finished in 10th place, eight seconds behind Cavagna and three behind Valverde, who is second overall.
The crash saw Roglic’s team-mate, former world time trial champion Tony Martin, forced to abandon the race after receiving medical attention.
Stage 20 on Saturday – the penultimate day of the race – is a 190.4km mountain stage from Arenas de San Pedro to Plataforma de Gredos.
Vuelta a Espana – stage 19 result
1. Remi Cavagna (Fra/Deceuninck – Quick-Step) 3hrs 43mins 34secs
2. Sam Bennett (Irl/Bora Hansgrohe) +5secs
3. Zdenek Ņtybar (Cze/Deceuninck-Quick-Step) Same time
4. Philippe Gilbert (Bel/Deceuninck-Quick-Step)
5. Alejandro Valverde (Esp/Movistar Team)
6. Tosh Van der Sande (Bel/Lotto-Soudal) +8secs
7. Dylan Teuns (Bel/Bahrain-Merida) Same time
8. Tadej Pogacar (Slo/UAE Emirates)
9. Miguel Angel Lopez (Col/Astana)
10. Primoz Roglic (Slo/Jumbo-Visma)
1. Primoz Roglic (Slo/Jumbo-Visma) 75hrs 0mins 36secs
2. Alejandro Valverde (Esp/Movistar) +2mins 47secs
3. Nairo Quintana (Col/Movistar) +3mins 31secs
4. Miguel Ángel Lopez (Col/Astana Pro Team) +4mins 17secs
5. Tadej Pogacar (Slo/UAE Emirates) +4mins 49secs
6. Rafal Majka (Pol/Bora Hansgrohe) +7mins 46secs
7. Wilco Kelderman (Ned/Sunweb) +9mins 46secs
8. Carl Fredrik Hagen (Nor/Lotto-Soudal) +11mins 50secs
9. James Knox (GB/Deceuninck-Quick-Step) +13mins 20secs
10. Marc Soler (Esp/Movistar) +21mins 9secs