@ErichPryde
Indeed rules have been relaxed during the STS space shuttle program
.
First Rolex in space?
Depends on the definition of space, for military test pilots this was 50 miles...
So the very first Rolex in space was a Rolex GMT-master 1675 Pepsi bezel pilot watch worn by test pilot William "Pete" Knight during
X-15 flight 190 (17 OCT 1967 reaching 85 kilometers).
Knight had also worn his Rolex GMT-master during X-15 flight 188 (03 OCT 1967 reaching a speed of Mach 6.7 or 7232 km/hour)!
.
The first automatic chronograph in space was a double win:
The very first automatic chronograph in space was a joint win, as during the 84 days long Skylab 4 mission (Nov 1973 - Feb 1974), both Commander Gerald Carr, 40mm
Movado Datachron HS360, and pilot William Pogue, 41mm
Seiko 6139-6005, wore an automatic chronograph !
The very first automatic chronograph directly exposed to the harsh vacuum environment of outer space, was the 38mm Fortis Official Cosmonauts chronograph, Lemania 5100 movement, worn by Mir-16 cosmonauts Yuri malenchenko and Talgat Musabayev (9 SEP 1994) !
See:
https://www.hodinkee.com/magazine/snuck-into-space