September 15, 1968 – Soviet Union launch Zond 5

Zond 5, a member of the Soviet Union’s Zond program, was launched from a Tyazheliy Sputnik (68-076B) in Earth parking orbit to make scientific studies during a lunar flyby and to return to Earth. On September 18, 1968, the spacecraft flew around the Moon.

Source: Wikipedia

Descent modules of Zond-5 (left) and Soyuz-3 (right)