[4] Phinney specialized in time trials on the road as well as the individual pursuit on the track, winning the world title in the discipline in 2009 and 2010.

[11] His early target for the 2012 season was the opening stage of the Giro d'Italia, which he duly won to wear the leader's jersey, the maglia rosa, becoming just the third American to do so following Andrew Hampsten in 1988 and Christian Vande Velde in 2008.

Phinney then switched his focus to the Olympic Games, targeting the road race and time trial, where he finished fourth in each event.

"[12] Phinney later explained his comment by stating that although legal, caffeine pills and mild painkillers were often used in the peloton during races, and that some riders even crushed them and mixed them in water bottles.

[12] On the penultimate stage of the 2013 Tirreno–Adriatico, in heavy rain, Phinney found himself well in arrears of the leaders on a tough finishing circuit, which included a climb at Sant'Elpidio a Mare with gradients reaching 27 percent.

In the early part of the 2014 season, Phinney won the inaugural Dubai Tour after winning the opening time-trial.

Two days later, at the United States National Road Race Championships, Phinney suffered a career-threatening crash after sliding into a guard-rail.

Phinney never wore his national jersey as he remained out of action for a year, having initially been given a six-to-eight-week recovery period.

[17] He competed at the Olympics, but despite entering the road time trial with hopes of a medal, he finished 22nd, over five minutes behind winner Fabian Cancellara.

[18] In September 2016 Phinney confirmed that he had agreed an initial two-year deal with Cannondale–Drapac from the 2017 season, with a focus on competing in the classics and aiming to race in the 2017 Tour de France.