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Umbreon @ none
Ability: Synchronize
Faint Attack
Moonlight
Shadow Ball
Iron Tail

I evolved him in Pokémon Sapphire and traded him to LeafGreen for training, so Gen 3 items only.

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Overall, I would say Leftovers is a good option for Umbreon. With Moonlight, it provides plenty of recovery to stall your opponents and deal passive damage. One suggestion to make this work better, I would do Toxic instead of Iron Tail. 75 accuracy isn't that good. Toxic with Moonlight gives plenty of time to stall your opponents out. Also, if you go with my suggestion, swap Shadow Ball for Protect for even more stalling and recovery, but is optional.
Hope I helped!

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Thanks! I was considering the Black Glasses just to boost his weak Dark-type move, but Leftovers make more sense. Thanks for helping out!
No problem.  Glad to help!
Leftovers and choice band are the only good items in gen 3. Every Pokemon that knows any non-physical moves should hold leftovers.