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In November 2019, Cummings announced his retirement from professional cycling.

During the 2017 Tour of the Basque Country Cummings crashed heavily and required surgery. After a long period of recovery he won both the British National Time Trial Championships and the British National Road Race Championships on the Isle of Man, becoming only the second rider to win both titles in the same year after David Millar achieved the same feat in 2007.

In July 2016 he was added to Great Britain's Olympic cycling team for the Summer Olympics, replacing Peter Kennaugh. Cummings took what British journalist William Fotheringham considered to be the most important stage race victory of his career to date at the Tour of Britain in September 2016. He finished 2nd on stage 2 in Cumbria, gaining a minute over most of his rivals. He subsequently moved into the lead on stage 6 and held this position for the remaining two days.

On 18 July 2015, Cummings won stage 14 of the Tour de France, beating French riders Thibaut Pinot and Romain Bardet in Mende, 1.5 km after the Côte de la Croix Neuve category 2 climb. It was the first Tour de France stage win for both Cummings and his African team MTN–Qhubeka, fittingly coming on Nelson Mandela Day. On 8 July 2016, Cummings took another breakaway win in the Tour de France, this time on Stage 7, with a winning margin of 65 seconds over Daryl Impey and Daniel Navarro.

In October 2014, Cummings announced that he would be joining MTN–Qhubeka for the 2015 season.

In September, Cummings finished second overall in the Tour of Britain. Later that month he announced he would join BMC Racing Team for the 2012 season.

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 (2.5 mi) to race, creating a gap. He held on to his lead and won by four seconds over the two chasers, Cameron Meyer of Orica–GreenEDGE and Team Sky's Juan Antonio Flecha.

In 2011, racing with Sky, he had arguably his most successful professional race to date at the Tour of Algarve. He won stage three in a mountain-top finish ahead of Alberto Contador, taking the overall lead of the race which he held until the final time-trial; he finished the tour in seventh place.

Cummings was part of the Great Britain team that helped Mark Cavendish win the 2011 UCI World Road Race Championship. He then finished 4th overall in the first Tour of Beijing.

Cummings joined new British-based Team Sky for the 2010 season.

His first professional win was in 2008, stage 2 of the Giro della Provincia di Reggio Calabria.

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 won the team pursuit at the 2005 UCI Track Cycling World Championships in Los Angeles and at the 2006 Commonwealth Games in Melbourne. He also took bronze in the individual pursuit at the 2006 Commonwealth Games. At the 2004 Olympics in Athens Cummings and the Great Britain team won the silver medal in the team pursuit and achieved a time of 3:59.866 in the heats.

In 1999, riding for Birkenhead North End CC as a junior, aged 17, Cummings won the Eddie Soens Memorial Road Race, a handicap race open to all categories. It remains the only time in 46 years that a junior has won. He went on to take the junior British National Road Race Championships that year.

Stephen Philip Cummings (born 19 March 1981) is an English former racing cyclist, who rode professionally between 2005 and 2019 for the Landbouwkrediet–Colnago, Discovery Channel, Barloworld, Team Sky, BMC Racing Team and Team Dimension Data squads.