I believe that #1 is a round of .22 Winchester Automatic
, a cartridge introduced for, and only usable in, the pioneering Winchester Model 1903 semi-auto rifle.
At the time, much of the .22LR ammo on the market was loaded with black powder, which would cause excess fouling and jam a .22LR semi-auto after a few shots. Winchester's solution to this potential reliability problem was to create an incompatible proprietary smokeless-powder-only round. Neither the rifle nor the round met Winchester's sales expectations, so they subsequently redesigned the rifle to take .22LR, renamed it as the Model 63, and dropped the Model 1903.
The round has been out of production for decades, relegating many Winchester Model 1903's to wall-hanger status.
I believe that #2 is a round of .32 Long Colt
, an outside-lubricated late 19th century contemporary to .32 S&W Long, but with a heeled bullet and a smaller-diameter case. The S&W round was far more successful, and most major commercial ammo companies dropped .32LC by the late 1960s.