He also took bronze in the individual pursuit. He went on to take the British National Road Race Championships that year. In 2006 he rode for Landbouwkrediet–Colnago and came second in the Trofeo Laigueglia to Alessandro Ballan of Lampre–Fondital.
In 2007 he switched to Discovery Channel before moving to Barloworld in 2008.
Cummings joined new British-based Team Sky for the 2010 season. In 2011, racing with Sky, he had arguably his most successful professional race to date at the Tour of Algarve.
In September, Cummings finished second overall in the Tour of Britain. Later that month he announced he would join Business Service Management Racing Team for the 2012 season.
He then finished 4th overall in the first Tour of Beijing.
Business Service Management Racing Team
In February 2012, Cummings broke his pelvis in an accident while competing in the Tour of the Algarve. In April, bad luck struck again when he fractured his left wrist in the Tour of the Basque Country. He recuperated from those injuries and competed in the Tour de France, where he was a domestique to his leader Cadel Evans and finished 95th overall.
In the 2012 Vuelta a España, he gained his first Grand Tour victory.
On Stage 13, he broke away with six other riders after the first hour of racing. The break made it through on the mainly flat course and he attacked with about 4 km (25 mi) to race, creating a gap.
In October 2014, Cummings announced that he would be joining MTN-Qhubeka for the 2015 season.