Danny Pate and Lars-Petter Nordhaug were among the attackers for Team Sky at the Giro dell'Emilia while Thomas Löfkvist saw his hopes dashed with one lap to go.
The Pate and Nordhaug both hit out in the prestigious Italian one-day event on a day where the team were unlucky not to influence the final result.
A coming together heading into the final lap saw in-form Löfkvist, who would eventually finished 20th, sidelined with a jammed chain at a key moment.
Pate had infiltrated a significant early move as 19 riders went clear, opening out an advantage of over one minute but were not allowed to remain out front.
Later Nordhaug also tried his luck as he briefly jumped clear of the peloton as the day's eventual break was set to be reeled in.
In the end it was Nairo Quintana who hit out in the closing stages to take an impressive victory, the Colombian rising star (Movistar) attacking out of a strong group of four riders in the final kilometre to stay clear to the line.
Quintana escaped the clutches of Fredrik Kessiakoff (Astana) and Italian national champion Franco Pellizotti (Androni-Giocattoli), the pair rounding out the podium positions following a grandstand finish.
As predicted the race was shaped by the ascent of the San Luca climb, a larger group of in-form climbers coming together ahead of the final lap before splinter attacks exposed the strongest riders.
The strain of the finishing circuit had seen the peloton begin to split apart as the race headed into the closing stages in Bologna.
The win for Quintana continued a season of strength for Colombian riders in the peloton, an attack spearheaded in part by Team Sky pairing Rigoberto Urán and Sergio Henao.
As the race got under way 19 riders headed up the road early on, Pate among the participants in a move which featured the majority of teams in the race
With the move deemed too dangerous and shut down there was a general regrouping before Damiano Caruso (Liquigas-Cannondale), Marco Marzano (Lampre-ISD), Paolo Tiralongo (Astana) and Giairo Ermeti (Androni-Giocattoli) combined to go clear.
The strong quartet shook off the attentions of the peloton to build up a buffer as they entered the Rocca di Roffeno circuit, ultimately taking 7:00 on the chasing pack following the Passo Sella della Croce.
Eventually the gap began to come down quickly, Farnese Vini and Saxo Bank-Tinkoff Bank among the teams pulling hard on the front as the pace intensified.
The break found themselves all but swept up as the race entered the 9km finishing circuit featuring the tough San Luca climb.
Fabio Aru (Astana) and Emanuele Sella (Androni-Giocattoli) were quickly on the attack but it would be the move of Quintana which proved most significant at the finish.
After the stage Sports Director Sean Yates explained the situation which took Löfkvist out of the equation late on.
“We knew Thomas was in good shape and motivated along with Lars-Petter," he said. "We are here with five riders after a long season but we had the gameplan to help those guys.
“Danny got in the early move which was good as we didn’t have to chase. That came back and then the remnants of the break were chased down.
“The finishing circuits were evil but we had Thomas up there. He was unlucky that he had his rear derailleur knocked with one lap to go and wrecked his chain. There were only around 13 riders left and he was in there so that was some bad luck for him.
“We came around the corner and he was there with his chain in between the 25 sprocket and the spokes. So that was a shame as he wasn’t able to get back on. Coming into the last descent there were only around 10 guys left and I’m sure Thomas could have taken a top 10.”