At the trials for the 1948 Summer Olympics, however, Dillard failed to qualify for the 110 m hurdles event, though he qualified as third (and last) for the 100 m, not his specialty.
At the Games, Dillard reached the final, which seemed to end in a dead heat between Dillard and another American, Barney Ewell. The finish photo showed Dillard had won, equalling the World record as well. This was the first use of a photo finish at an Olympic Games. As a member of the 4 x 100 m relay team, he won another gold medal at the London Games.
Four years later, still a strong hurdler, Dillard did qualify for the 110 m hurdles event, and won the event in Helsinki. Another 4 x 100 m relay victory yielded Dillard's fourth Olympic title.
Dillard attempted to qualify for a third Olympics in 1956, but failed.