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rather go with this:
Felder vs. winner of Iaquinta-Hooker (UFC 243)
Gillespie vs. Islam Makhachev or Charles Oliveira
Gillespie vs. Makhachev would be great to see how a elite D1 wrestler stacks up against a Dagestani with a legit sambo/wrestling background
Gregor vs Islam would be super fun, but generally (not always, but usually) the UFC holds off on matching up prospects as long as possible. They'd rather have the newer guys (I'm saying "newer" because Gregor isn't that young--although he doesn't have a lot of MMA miles on him) fight the older guys who were contenders but who are slipping a bit. Or at least guys who are established and not considered "prospects" anymore.
The Oliveira fight makes more sense though, I like that. Ranked right next to each other, and it will show how Gregor deals with a real submission threat on the ground. Won't answer every question by a long shot but it will show some things for sure.