This is an interesting concept and one that I've often wondered about - if you have two weapons systems from two different historical timeframes, could they actually engage each other? I'm thinking not of a 300, but say a Sopwith Camel or even an archer with longbow. I'm not saying they could do any damage, but could they even be detected and given the relative speeds, could they be engaged?
But to get back to the original question, I wonder why drones aren't one of the main battlefield weapons at this point - not a huge UAV, but a $1000 DJI Phantom or something similar. Sure the payload wouldn't be great, but does it need to be if it can find a three mile long convoy, hover in front of the windshield of the first vehicle and explode?
I'm also surprised they haven't been used more extensively for assassination attempts. We already have plexiglass walls surrounding people giving speeches, but there's no plexiglass roof, AND the coordinates should be already known, so no need to have a jammable control signal. That just seems like a logical next step, becaause it seems like everything humans invent sooner or later gets turned into a weapons system, aircraft being the perfect example