You messed up and re-typed things like 22 and 23 again after 23, in case there's confusion. I'm just going in order.
I want to bump this solely because of the discussion potential, but it is also confusing with all of these matchups. Fortunately, they are just one-on-ones, so it shouldn't be too befuddling.
1. Sam. Too much explaining. I'd prefer Dean.
2. Not sure, to be honest. I'll call it a draw.
3. Azazel, probably pretty easily.
4. Azazel - with more difficulty than the last, perhaps, but not much more.
5. Lilith in a good fight.
6. Eh... Crowley, pretty easily.
7. Hmm.. good fight. Azazel might be more powerful?
8. Crowley without too much issue.
9. I'd probably go for Dick Roman, even though theoretically, Eve is more powerful. I might just call it a stalemate because neither has shown the capacity to necessarily kill the other, but it's not implausible that they could do that.
10. Stalemate, because Phoenix's powers aren't enough to match up to Eve, but Phoenix Ash kills her.
11. Dick Roman is vastly more powerful. Phoenix simply cannot defend itself from getting consumed by any Leviathan.
12. DR stomps.
13. Again, Dick Roman stomps. No demon can stand up to a Leviathan.
14, & 15. Dick Roman SLAUGHTERHOUSE.
16. The sheer numbers would make it harder, but unless they actually possess the bone, they can't really beat him because permanent Death is the only option. Dick still wins.
17. Castiel impressed me more.
18. Raphael should be more powerful. H2H - probably just a who strikes first scenario, and they win via stabbing the other with an archangel blade.
19. Michael, slightly.
20. Hmm. Lucifer is more powerful than either individually, but together... eh. They should be able to win.
21. Probably Jesse Turner. Raphael has more overall feats, and is more diverse, but even though he is extremely powerful, he hasn't really displayed the level of reality warping such as turning angels into toy figures. Holistically, I'd give it to Jesse, but in terms of overall feats, Raphael is better.
22. Gabriel has some pretty good reality warping feats (making a fake archangel blade from a soda can, creating his own world, etc.). Holistically, I'd favor Jesse, but from feats, probably Raphael.
23. I really doubt Jesse could win a single round against them both.
24. Well, Jesse needs Lucifer to have his powers. Weird fight. Lucifer should get it, though.
25. Yeah, probably Michael. Not a stomp, but likely a plain victory.
26. All four archangels at once against Jesse? Archangels SLAUGHTERHOUSE.
27. Hmm... War could win because of Famine's current condition - as far as manifestations go, Famine appears the weakest as a result of vast agricultural improvements, which have reduced the rate of famine severely. Famine could feasibly win on the account of.... better showings, for one, and being older. I know being older intrinsically means nothing, but the general rule in SN is that the older you are, the more powerful you are. Famine is, as far as can be inferred, older than War. However, Famine doesn't actually manage to beat War in that sense. I doubt an abstract entity would hunger for anything - though War could hunger for war, but Famine has no win conditions. Neither does War, so I guess it's a stalemate.
28. Well, Pestilence has good showings and all, but he can only affect humans (since they are the only beings whom have displayed a susceptibility to illness). He did affect a low-powered angel, but a depowered angel can't really compare with an abstract entity. Pestilence can't affect War - War can't really win either. Stalemate again.
29. Neither Famine nor Pestilence can do anything to the other. Logically, Famine can't devour Pestilence, and he really can't do anything else to him, and Pestilence can't afflict an abstract entity with physical illness. Again, stalemate.
30. Death stomps. He is clearly the oldest and most powerful of the Horsemen, and he actually can reap them all, especially if he has the capacity to reap God (not confirmed, of course, but it's not impossible). At least this is a stalemate, because none of the Horsemen can actually afflict Death with anything. Death isn't susceptible to any of their powers. Whereas they simply cannot defend themselves from Death reaping them, ie with his Scythe.
31. Death SLAUGHTERHOUSE. No reasoning required.
32. Jesse managed to turn a regular Castiel into a toy figure, but Soul-Gorged Castiel literally obliterated Raphael, a good match for Jesse, with a snap of his fingers. Castiel SLAUGHTERHOUSE.
33. Well, it was one snap of his fingers for Raphael's obliteration, this time it'll be two snaps. Castiel slaughterhouse again.
34 and 35. Yeah, I extremely doubt that Lucifer or Michael could destroy Raphael so easily. They might be more powerful, but Raphael is at least a good match for them. If Castiel doesn't slaughterhouse, he should at least stomp.
36. Facing them both at once still shouldn't be a real challenge. With all the millions of souls in Purgatory, as well as all the Leviathans inside him, Castiel should stomp.
37. All 4 Archangels might give Castiel momentary pause at best, but get destroyed at worse. Castiel, 10/10.
38, 39, 40 and 41. Death obliterates.
42. Death still stomps. I'm inclined to say the numbers don't matter. If Soul-Gorged Castiel was a fly to Death, then an archangel should be a worm. Four worms vs Death. Death obliterates again.
43. Already done, Death destroys him with a gesture.
44. Death considered swatting Castiel to be like swatting a fly, and logically, Death is more powerful. So I guess Death reaps "God" for 10/10.
You have too many mismatches. Better fights which you didn't consider would have been ideas such as Horsemen vs Archangels, Horsemen vs Leviathans, Archangels vs Leviathans, Eve vs varying Horsemen and Archangels individually, etc.
You didn't include several characters such as Seraph Castiel, Uriel, Zachariah, Atropos, etc. With the newer seasons, characters like Cain, Metatron, Abaddon, Naomi etc. should also be used, although understandably this couldn't have occurred this far back.
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