One possible plot twist could be that Pennywise actually has a fear of bats, which gives Batman an unexpected advantage. Another could be that Pennywise manages to possess Batman and uses his skills and resources to wreak havoc in Gotham, but Batman's consciousness fights back from within. Or perhaps there's a plot twist where the two form an unlikely alliance to fight a greater evil that is threatening both their existences.
One possible storyline could be that Goku is accidentally transported to Alucard's world. They start off as enemies but then gradually learn about each other's powers and come to respect one another. Another could be that a powerful villain manipulates them into fighting each other. In this case, they might realize they are being used and team up against the real enemy.
It's really hard to say. Goku is extremely powerful with his Super Saiyan forms and incredible combat skills. But Alucard has his vampiric powers like immortality and the ability to control shadows. In a fanfic, it could go either way depending on how the author wants to write it. Maybe if the author wants to emphasize speed, Goku might have an edge. But if it's about dark, mysterious powers, Alucard could come out on top.
Batman would likely have the upper hand in a battle of wits. He's a master detective with years of experience analyzing foes and coming up with strategies. However, Pennywise thrives on fear, and his ability to manipulate the environment and a person's worst nightmares is a powerful weapon. But Batman has faced his own inner demons and has the willpower to resist Pennywise's fear tactics. So, overall, Batman might be able to outsmart Pennywise and find a way to defeat him.
There could be a storyline where Issei challenges Goku to a friendly sparring match to test his own limits. As they fight, they exchange techniques and learn from each other. This could lead to Issei unlocking new forms of his own power, inspired by Goku's Super Saiyan forms. And Goku could also gain new insights into combat from Issei's more unorthodox fighting style.
It depends on the rules set in the fan - fiction. If it's a battle based on strategy, Issei might have a chance. He has shown to be quite cunning in his battles. But if it's a pure power - based fight, Goku has the upper hand. His years of training under various masters and his Saiyan heritage give him an edge. Also, Goku has experience fighting opponents much stronger than himself and finding ways to overcome them.
Obviously, Pennywise is one of the main characters. He is the terrifying clown that haunts the story. And then there are the kids who are the protagonists. They are the ones who have to face Pennywise and try to overcome their fears.