10 most painful Grand Slam defeats for Roger Federer

#1 2019 Wimbledon final: Djokovic beat Federer 7-6(5) 1-6 7-6(4) 4-6 13-12(3)

Djokovic saves two championship points on the Federer serve to prevail in historic deciding set Wimbledon tiebreak

Federer won 14 more points, had a better serve percentage in the match, won more points at the net and broke his opponent 7 times (to being broken thrice), but it mattered not in the final scheme of things as three tiebreaks in the match, including a first ever deciding set tiebreak at 12-all in the fifth, went Djokovic's way.

When Federer broke Djokovic at 7-7 in the fifth and arrived at two championship points on serve at 40-15, the headlines screamed, "Federer prevails over Djokovic in battle royale to win ninth Wimbledon title."

A 21st Grand Slam title, however, agonisingly slipped out of Federer's grasp as the Serbian stunned Centre Court to break Federer back and prevailed 7-3 in the first ever Wimbledon deciding set tiebreak at 12-all, to deny the Swiss a historic ninth title in the longest ever Wimbledon final spanning 4 hrs 57 mins.