Cosmonaut Georgy Beregovoy blasted off in Soyuz 3, October 26, 1968 to rendezvous with Soyuz 2, an unmanned craft which was launched the previous day. Beregovoy tried to dock with Soyuz 2 twice but failed on both attempts. He came within 660ft to his target.
The mission was considered a success though since he was able to rendezvous with another craft. At least, that's what the Soviets said.
At the time, Beregovoy was the oldest man to go into space, at the ripe old age of 47.