This investigation describes the sprint performances of the highest internationally ranked professional male road sprint cyclist during the 2008-2011 Grand Tours. Sprint stages were classified as won, lost, or dropped from the front bunch before the sprint. Thirty-one stages were video-analyzed for average speed of the last km, sprint duration, position in the bunch, and number of teammates at 60, 30, and 15 s remaining. Race distance, total elevation gain (TEG), and average speed of 45 stages were determined. Head-to-head performances against the 2nd-5th most successful professional sprint cyclists were also reviewed. In the 52 Grand Tour sprint stages the subject started, he won 30 (58%), lost 15 (29%), was dropped in 6 (12%), and had 1 crash. Position in the bunch was closer to the front and the number of team members was significantly higher in won than in lost at 60, 30, and 15 s remaining (P < .05). The sprint duration was not different between won and lost (11.3 ± 1.7 and 10.4 ± 3.2 s). TEG was significantly higher in dropped (1089 ± 465 m) than in won and lost (574 ± 394 and 601 ± 423 m, P < .05). The ability to finish the race with the front bunch was lower (77%) than that of other successful sprinters (89%). However, the subject was highly successful, winning over 60% of contested stages, while his competitors won less than 15%. This investigation explores methodology that can be used to describe important aspects of road sprint cycling and supports the concept that tactical aspects of sprinting can relate to performance outcomes.