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For Gildarts Clive vs Gray Fullbuster, the match will really come down to pure speculation...
Gildarts was definitely the strongest Fairy Tail Member before the timeskip and still probably holds that title but there is really no way of knowing for sure. From portrayal, Natsu couldn't even push Gildarts into being serious when they fought pre-timeskip.
So, if Gildarts didn't train, I would place the difficulty at Extreme Difficulty. If he did, then it would probably be Medium Difficulty. That is why I settled with High Difficulty in the end.
- Gildarts > Gray [High Difficulty]
Gildarts was definitely the strongest Fairy Tail Member before the timeskip and still probably holds that title but there is really no way of knowing for sure. From portrayal, Natsu couldn't even push Gildarts into being serious when they fought pre-timeskip.
So, if Gildarts didn't train, I would place the difficulty at Extreme Difficulty. If he did, then it would probably be Medium Difficulty. That is why I settled with High Difficulty in the end.