Jakob Fuglsang (Astana) rode to a first ever individual Grand Tour stage victory at 34 years of age, with Tao Geoghegan finishing a disappointed runner-up for the second time at this year's Vuelta a España.
Another Brit, James Knox (Deceuninck - Quick-Step) was involved in the action until the final few kilometres until he eventually cracked and rode across the line in fourth place.
Miguel Ángel López was the second Astana man to go on the offensive as he attacked the GC riders, taking Tadej Pogačar (UAE Team Emirates) and race leader Primož Roglič (Jumbo-Visma) with him.
Alejando Valverde (Movistar) lost time to the 20-year-old Slovenian, who will have a couple more opportunities to try and dislodge the world champion from his second place on GC.
James Knox's performance saw him rise six places on GC to 11th, now sitting just 1-21 outside the top 10.
Tomorrow sees the second and final rest day of this year's Vuelta, the race resuming with a stage 17 that is unlikely to bother the GC riders.
How it happened
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Another tough mountain day beckoned on stage 16, with only two more big days following this one, and as the chances for GC contenders tick down those with nothing to lose will grow more desperate for a result.
Stage 16 provided two first category warm-ups before the real test of the day, the HC summit finish up to Alto de La Cubilla.
Route profile map of stage 16 of the Vuelta a España 2019
Multiple attacks were launched after around 10km of racing, before Deceuninck - Quick-Step's sole British rider James Knox stretched his legs at the 27km mark. The peloton all came back together after 36km but then four riders went off the front of the peloton, with Knox making the selection once more.
Ag2r La Mondiale's Geoffrey Bouchard beat Ángel Madrazo (Burgos-BH) to the summit of the first category one climb of the day, the Puerto de San Lorenzo, with the Frenchman taking the lead in the King of the Mountain classification off the Spaniard.
The same one-two result was repeated up the Alto de la Cobertoria, as Bouchard opened up a six point gap over Madrazo, as Thomas De Gendt (Lotto-Soudal) attacked the breakaway, reaching the intermediate sprint with 27km to go ahead of Philippe Gilbert (Deceuninck - Quick-Step) and Bouchard.
With 20km remaining, before the final summit climb, the large breakaway did briefly split up, but all came back together with the peloton trailing by nine minutes.
This deficit meant that not only would the stage winner come from the large group of escapees, but also that Knox stood to rise up the GC by quite a way, and was supported by his Deceuninck - Quick-Step team-mates Gilbert and the Frenchman Rémi Cavagna.
With 13km to go, the gap wasn't coming down very quickly at all, as the GC riders appeared to have reached a stalemate. Sunweb's Wilco Kelderman, who sits in eighth on GC, received assistance from a team-mate as he dropped from the peloton, showing the severity of the pace being set as Jumbo-Visma neutralised any attacks, with six of their riders on the front.
With 9.5km to go, five riders peeled off the front of the breakaway. Knox, Tao Geoghegan Hart (Ineos), Jakob Fuglsang (Astana), Gianluca Brambilla (Trek-Segafredo), were led by Luis León Sánchez (Astana).
As Sánchex cracked with just over 7km to go, Fuglsang pushed on, with only Brambilla able to keep his wheel. Knox and Geoghegan Hart then banded together, trying to make their way back up to the front of the race.
By 6km to the line, Fuglsang and Brambilla had opened up a gap of 12 seconds, with the Dane doing all of the pulling on the front to keep the Brits at bay, with Geoghegan Hart sitting on Knox's wheel.
Astana were also animating the race behind, as Omar Fraile upped the pace on the front of the peloton with López aiming to displace Tadej Pogačar in third, as Nairo Quintana (Movistar) fell away from the group.
Fuglsang then took flight and Brambilla was reeled in by the British contingent, with Geoghegan Hart then countering, going off in pursuit of the Dane.
López then tried to ride off the front of the GC group, as Pogačar and Roglič immediately jumped on his wheel, with Movistar's Marc Soler leading Alejandro Valverde and Rafał Majka (Bora-Hansgrohe) up the climb as the rest fell away.
As the mist descended, Fuglsang was less than 2km from the summit, with a 16 second advantage over Geoghegan Hart, who was digging deep to try and avoid another second place on a 2019 Vuelta stage.
Meanwhile, López went again as Pogačar stayed with him and Roglič lost the wheel. Valverde then cracked, with Soler waiting for him to offer assistance to the world champion.
With Majka on his wheel, Roglič took it upon himself to chase down Pogačar and López, his Jumbo-Visma lieutenants long gone.
Through the mist as the time counter ticked over the four hour mark, Fuglsang emerged, checking behind him to guarantee his first ever individual Grand Tour stage victory.
Geoghegan Hart then crossed the finish line second, 26 seconds later, with Sánchez and Knox following soon after.
Back in the GC race, Roglič managed to ride back up to Pogačar and López, with the young Slovenian doing the work to put more time into Valverde, chipping away at the Spaniard's advantage.
Imanol Erviti (Movistar) was swept up and worked hard for the Valverde group, which had the added effect of helping Majka chew into Quintana's time, eventually losing the Colombian his GC position to the Pole by three seconds.
Pogačar saw the line and sprinted for it, with López and Roglič in his wheel as they finished six minutes down on Fuglsang. Valverde then came across the finish line, having lost 23 seconds to Pogačar.
Results
Vuelta a España 2019, stage 16: Pravia to Alto de La Cubilla Lena
1. Jakob Fuglsang (Den) Astana, in 4-01-22
2. Tao Geoghegan Hart (GBr) Ineos, at 22 seconds
3. Luis León Sánchez (Esp) Astana, at 40s
4. James Knox (GBr) Deceuninck - Quick-Step, at 42s
5. Gianluca Brambilla (Ita) Trek-Segafredo, at 1-12
6. Thomas De Gendt (Bel) Lotto-Soudal, at 2-09
7. Mikel Bizkarra (Esp) Euskadi Basque Country - Murias, at 2-15
8. Amanuel Ghebreigzabhier (Eri) Dimension Data, at 2-21
9. Philippe Gilbert (Bel) Deceuninck - Quick-Step, at 2-32
10. Geoffrey Bouchard (Fra) Ag2r La Mondiale, at same time
General classification after stage 16
1. Primož Roglič (Slo) Jumbo-Visma, in 62-17-52
2. Alejandro Valverde (Esp) Movistar, at 2-48
3. Tadej Pogačar (Slo) UAE Team Emirates, at 3-42
4. Miguel Ángel López (Col) Astana, at 3-59
5. Rafał Majka (Pol) Bora-Hansgrohe, at 7-40
6. Nairo Quintana (Col) Movistar, at 7-43
7. Nicolas Edet (Fra) Cofidis, at 10-27
8. Wilco Kelderman (Ned) Sunweb, at 10-34
9. Carl Frederik Hagen (Nor) Lotto-Soudal, at 10-40
10. Hermann Pernsteiner (Aut) Bahrain-Merida, at 12-05
Others:
11. James Knox (GBr) Deceuninck - Quick-Step, at 13-26
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Jonny was Cycling Weekly's Weekend Editor until 2022.
I like writing offbeat features and eating too much bread when working out on the road at bike races.
Before joining Cycling Weekly I worked at The Tab and I've also written for Vice, Time Out, and worked freelance for The Telegraph (I know, but I needed the money at the time so let me live).
I also worked for ITV Cycling between 2011-2018 on their Tour de France and Vuelta a España coverage. Sometimes I'd be helping the producers make the programme and other times I'd be getting the lunches. Just in case you were wondering - Phil Liggett and Paul Sherwen had the same ham sandwich every day, it was great.
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