With all the crazy potential matchups I could think of, Jeepers Creepers going one on one with a Predator was very interesting to me. On one hand I'm probably completely biased, since I've been a big time Predator fan since the mid 80s.
Now based on fairness, if these two battled, it would be somewhere familiar for the demon, not the Predator, since the Demon only hunts in a certain area every 23 years I believe. So the country is where they would most likely fight, since the Predator would definitely be hunting Jeepers Creepers.
Jeepers Creepers has several advantages going into this battle, including regeneration and flying. But unfortunately for the demon, he needs to feed and take parts from other living beings in order for that to happen. The Demon also has custom weapons like knives, throwing stars, and axes that are made from bone and skin from those hes hunted and eaten. He can take some major damage and still keep coming. His major advantage is flight in this fight and the fact he can smell fear. Jeepers Creepers might have enough strength to pick up the Predator if he could get close enough.
The Demon from Jeepers Creepers is also quick, not just on foot, but his flying speeds. I really think his best chance would be up close and personal with the Predator, using his homemade weapons to pierce the Predators open areas, like his stomach.
The Demon is also smart enough to supe up his vehicle, create weapons, and has medical expertise to take whatever body part he wants from a human without killing them at first.
The Predator is a Hunter that most likely has no fear, so the Demon couldnt really sniff him out. With his helmet, he has cloaking tech that would get him close enough to the demon, especially with his stealth. His helmet also has enhanced vision which would make it difficult, almost impossible for the demon to hide or surprise him.
Predators strength varies but all of them are strong enough to toss a 300 pound human like it's nothing. Hes quick, but not faster than the demon.
Predators weapon, the plasmacaster, negates Jeepers flying, I dont even think with Demons speed that he can juke and move out of all the shoulder cannons shots, it would also surprise him that his weapon even exists.
Predator also has his netgun which can capture and kill his opponent if hit head on. I really dont think he would be able to escape that net.
Other weapons he would use is the wrist blade which in itself is deadly, especially up close. His retractable spear is also another deadly weapon that he would attempt to use against his deadly opponent. And if hes losing terribly and about to die, Predator can just self detonate and destroy himself and his opponent if he doesnt understand what's happening. So hes got a ton of other weapons, but it's not some comedy, he can't just fit it all in his pocket, so let's just assume that's all he has.
I think Predator verses Jeepers Creepers would most likely turn into a hand to hand battle, the Predators warrior instincts might kick in and it could turn into a pride thing to where the Predator would watch his opponent and then attack, but he would want a one on one battle to take the demons skull.
Jeepers would most likely try and attack from the air if such a creature threatened him, but unknowingly would swoop down to Predators cannons blasting his wings negating flight, leaving him with the option to fight close quarters.
Jeepers would use his throwing star that could actually hit Predator but again, with the blaster, I think he would knock it out of the air quickly, which would make the speedier Demon attack head on, which would be a mistake due to all Predators weaponry. Especially the gauntlet, which is a expanding like sword on his arm.
With Jeepers wings out of order I just couldnt see the demon coming out on top unless he managed to disable the Predators cannon. I think the Predators weapons would be to much of a surprise to the Demon, even if he was quicker.
So let's go down the list of who wins what if they battled:
Speed: Jeepers Creepers
Strength: Jeepers Creepers
Fighting ability: Predator
4-2 In Predators favor. Even with The demons speed and power, his main advantage would be flight and being able to regenerate after eating more humans. He wouldnt be able to regenerate and the plasmacaster would stop him from being able to fly. Predators weapons are to high tech and if it came down to a knife like fight, it would be bloody, but Predators expert fighting skill in the hunt would be enough to take down the Creeper.