Germany tested an air-launched an anti-ship UAV / guided missile in WWII.
Heck, I remember the Germans designing/prototyping a giant anti-battleship / infrastructure target shaped-charge warhead UAV based on the FW190 (!!) IIRC.
Here, was a FW-190 that would launch a JU88 full of explosives!
https://en.wikipedia.org/wiki/Mistel