Filippo Simeoni of Domina Vacanze won a two-man sprint finish to claim victory in stage 19 of the Tour of Spain on Friday.
Isidro Nozal, of the ONCE team, retained the overall lead but lost over a minute to US Postal rider and former Vuelta winner Roberto Heras, who moved up to second in the rankings.
Simeoni escaped in an early breakaway and edged out Danish rider Klaus Moller after just under four hours of riding.
Heras, who came in among a second group of riders 16 seconds adrift, moved into second at the expense of ONCE's Igor Gonzalez de Galdeano.
Heras, who has been a vital cog in Lance Armstrong's support team in the Tour de France for past three years, upped the pace on the day's final climb.
Nozal struggled to go with him and crossed the summit of the first category Navecerrada climb, which is 24km from the finish line, one minute 20 seconds behind.
Nozal's ONCE team regrouped around their young race leader and clawed back a few seconds, but Heras is now just 1:55 behind Nozal in the overall standings.
1. Filippo Simeoni (Ita) Domina Vacanze, three hours, 51 minutes, 18 seconds
2. Klaus Moller (Den) Milaneza, same time
3. Miguel Martin Perdiguero (Spa) Domina Vacanze, 0:16 behind
4. Cristian Moreni (Ita) Alessio, same time
5. Beat Zberg (Swi) Rabobank, same time
6. Felix Cardenas (Col) Labarca 2, same time
7. Unai Osa (Spa) iBanesto.com, same time
8. Michael Rasmussen (Den) Rabobank, same time
9. Alejandro Valverde (Spa) Kelme, same time
10. Roberto Heras (Spa) US Postal, same time
1. Isidro Nozal (Spa) ONCE, 65 hours, 13 minutes, 30 second
2. Roberto Heras (Spa) US Postal Service, 1:55 behind
3. Igor Gonzalez De Galdeano (Spa) ONCE, 3:03 behind
4. Alejandro Valverde (Spa) Kelme, 4:06 behind
5. Francisco Mancebo (Spa) iBanesto.com, 5:13 behind
6. Manuel Beltran (Spa) US Postal, 5:16 behind
7. Michael Rasmussen (Den) Rabobank, 6:11 behind
8. Luis Perez (Spa) Cofidis, 7:37 behind
9. Unai Osa (Spa) iBanesto.com, 7:43 behind
10. Felix Cardenas (Col) Labarca 2, 8:14 behind