The 2014 season was the first season that Rolland rode the Giro d'Italia. After a spring where he had not delivered any top results, the pressure was lifted off his shoulders as he started the race. After finishing 21st in the team time trial, Rolland started the Giro off in the worst way possible. However at the end of the first week, Rolland improved and he moved up to 12th overall when the second rest day approached. As the more mountainous stages appeared in the race, Rolland improved his performance and moved even further up in the general classification. On the stage to Val Martello, Rolland finished 3rd and moved up to 4th overall. He advanced to 3rd place just two days after, and despite delivering one of his best Time trials ever on stage 19 where Rolland finished 4th, he dropped out of the podium placings. On the penultimate stage to Monte Zoncolan, Rolland was on an almost impossible task, if he wanted to finish on the podium. He eventually lost 4 seconds to Fabio Aru, and therefore finished fourth in the general classification, his best finish in a Grand Tour. As he arrived at the Tour de France, Rolland was not considered any threat to the general classification and could therefore focus on breakaways. He attacked on stage 2 in the final kilometres but was unable to remain clear. On stage 9 to Mulhouse, Rolland moved up to 8th in the general classification after his performance in the breakaway. On the next day he dropped to 16th overall, possibly because of his efforts on the previous day. His best stage finish came on stage 17 to Saint-Lary-Soulan where he was 6th. Rolland finished the Tour de France just outside top 10, in eleventh overall.