10 most painful Grand Slam defeats for Roger Federer

#8 2014 Wimbledon final: Djokovic beat Federer ‎6–7(7–9), 6–4, 7–6(7–4), 5–7, 6–4

Federer poses with the runner-up trophy following a five-set loss to Djokovic in the 2014 Wimbledon final

Playing his first Slam final in two years, since his 2012 Wimbledon victory, the then 32-year-old Federer faced Djokovic in 2014 final, with a first opportunity to steer clear of William Renshaw and Pete Sampras and win a record eighth Wimbledon title. After a tight opening set edged out by Federer in a tiebreak, Djokovic won the following two sets and led 5-2 in the fourth before the Swiss won five games in a row to force a fifth. Federer's momentum would be stalled though as Djokovic regrouped to win 6-4 in the deciding set, for a second Wimbledon triumph. In his 25th Slam final and ninth at Wimbledon, seven-time champion Federer suffered an eighth defeat, for a second runner-up finish at the grass-court major.