So I'd say that It's a Raketa celebrating fifty years of anti aircraft defences around Leningrad.
*edit* Oops missed page one.
Looking at that, воздушной апмии means 'Air Army' and I'd say the piston aircraft is a Lavochkin La-5 which was arguably the Russians' best domestic aircraft of WWII, while the jet looks a lot like a Sukhoi Su-27 or Flanker as NATO call it. So putting the two together, I suspect it's celebrating these chaps as they are in the Leningrad area and had units that both flew the LA-5 in late '42 and the Su-27 in the nineties even if their designation changed a couple of times.
This would make sense as their designation changed several times between '42 and '92, making an army number difficult to apply so that's my best guess. It makes sense for a company desperately trying to make a feelgood connection with the great patriotic war.
ahem...
1-st one literally says 50 years of aerial army, which technically means 50 years of Air Forces 1942-1992
2-nd 50 years of Air Defense Forces of Leningrad 1942-1992.
I think both watches are commemorative edition dedicated to http://en.wikipedia.org/wiki/Siege_of_Leningrad one of the darkest episodes of WWII and Soviet Air Forces that fought against Nazis, protecting Leningrad.