Isshiki Ōtsutsuki vs Sam Winchester

Suggested by Anonymous Sam has seen a whole lot during his travels. He’s dealt with every kind of supernatural boss there is but he’s still not ready for this alien. Isshiki could wipe Sam off the face of the Earth with a single move and the guy would not have had any time to prepare a proper counter move. Sam would just end up being obliterated and that would be game over. Isshiki Ōtsutsuki wins.

Sam Winchester vs Hellboy

Suggested by Anonymous Sam has made it his business to go around taking out a bunch of demons like Hellboy over the years. He has obtained many supernatural abilities so it’s fair to say that he would give Hellboy a good fight. I just don’t see him being able to come out on top though. His fire abilities will be rendered useless here and even with his physical augmentations, Hellboy is stronger than Sam. This really puts Sam in a bind and it’s not one that I expect he will be able to get out of. I could see this being a close fight though and one that Hellboy would lose if he were to underestimate Sam. Hellboy wins.

Sam Winchester vs Angelus

Suggested by iKnowledge Time for Sam to return once more and grab another win. Angelus is a vampire and one who has a great deal of physical power. He’s not an opponent to take lightly, but Sam has been destroying guys like this for years. It would be relatively simple for him to stop Angelus in his tracks. There just isn’t much that Angelus would be able to do against him and that’s why Sam will have a considerable edge this time. Sam surpasses him in almost every stat. Sam Winchester wins.

Sam Winchester vs Phoebe Halliwell

Suggested by iKnowledge Sam and Phoebe are certainly no strangers to magic. Phoebe has augmented strength and defense as well as speed. She’s a capable all around fighter who may not be a fighter by nature but can really hold her own in a match. In the other corner you’ve got Sam who has so many powers it is hard to list them all. This fight really boils down to the fact that his healing factor is considerably better than Phoebe’s and he is a better fighter. She won’t be able to get past him. Sam Winchester wins.

Sam Winchester vs Randall Flagg

Suggested by iKnowledge Sam has returned once more. Randall Flagg is one of those characters who has a lot of vague cosmic abilities but rarely actually does things. Occasionally he does have some physical feats though like surviving a fatal gun wound and catching a bullet. The guy is definitely pretty tough, but I’d say that this is one demonic threat that Sam can overcome. His own abilities are quite versatile and potent. I don’t believe Randall will be able to keep up. Sam Winchester wins.

Sam Winchester vs Alistair

Suggested by iKnowledge Sam has returned and this time he is fighting someone from the Dragon Age series. Alistair is a skilled fighter with a blade. His shield can also be used for offense with his punishing charges. He would have had a good chance at Sam without the demonic enhancements, but with them there isn’t much he can do against Sam. Any blow he lands will have its damage healed very quickly. Sam can then finish Alistair off with his TK or fire abilities. Either way there is no escape. Sam Winchester wins.

Sam Winchester vs Mephisto

Suggested by iKnowledge Sam has a ton of experience dealing with high ranking demons. He was even able to resist Lucifer which is no small feat. Mephisto is about as high ranked as you can get for a demon though so you can’t even compare him to most. Mephisto has stood up to guys like Dr. Doom and Thanos in the past even if his results may not have been great. He certainly took a beating but his abilities are very real. I believe the sheer force of his energy projection abilities will be too much for Sam and will punch through his TK shield. Mephisto wins.

Sam Winchester vs Gajeel

Suggested by iKnowledge Sam Winchester is a pretty strong hunter. Not only is he very experienced, but he has been possessed before and has also been granted quite a few handy abilities. He has long range options as well as close ones. You don’t want to get anywhere near him id you’re most fighters. Gajeel definitely won’t be one of them though. He has gone up against Natsu in the past and his armor can block just about any attack that Sam throws his way. Gajeel just doesn’t go down very easily and his stats are all through the roof. Gajeel wins.

Sam Winchester vs Dean Winchester

Pac-Man Fever
It’s time for a double debut! Both of these characters are major players in the Supernatural series. They’ve both displayed a range of super powers, but it’s safe to say that Dean has a considerable edge over Sam. Dean’s abilities were really amped up when he became a knight and he has just about every useful ability. Telekinesis, Super Strength, Super Speed, Power over Earth, and a number of others. Sam has some limited telekinesis and a few of the other abilities, but his pre cog edge won’t really help here. Dean’s raw power is just on another level and Sam’s going to need a big boost of his own if he wants to win here. Dean Winchester wins.