Pete- Note that while the scans of these drawings come from the Winchester archives now housed at Cody, the two drawing in THIS thread are both Frankford Arsenal drawings by the Ordnance Department, so they could be totally unrelated to any Winchester commercial production. I do not know for sure if Winchester had any Army contract for this ammo.
Neither shows a jacketed bullet, only 500 grain (16 lead 1 part tin) unjacketed bullet.
The drawing for “Rifle Ball Cartridge Cal. .45 Model 1898 for smokeless powder” is dated February 25, 1898, which would be consistent with your F 4 98 example.
There is a separate thread with a WINCHESTER drawing of “Bullet of Service Rifle Ball Cartridge Caliber .45 Metal Patched” dated May 17, 1899. I know nothing about those, and what type of cases were intended for use with these. My original comment was only to note the fact that the two Frankford Arsenal drawings covered both smokeless and black powder loads.