>>44970279Here are the following hardest matches that come to my mind, in no particular order:
a. Battle Frontier in Platinum/HGSS;
b. Battle Frontier in Emerald (difference is some of the enemy movesets sucked too much);
c. Necrozma without special strategies (with a common playthrough team);
d. Cynthia without proper pre-league training;
e. Red in Silver/Gold (because movesets were shittier in Gen 2);
f. BW2 hard mode rematch with Iris (also depending on how leveled up you are);
g. Gen 6 Battle facility: because those shitters are straight up stealing, I've never had so many evades and sheer colds hitting;
h. G-Max without Lvl 100 and the other guys with a combination of Solrock + Wobbufett + Togepi. Unless you're overleveled and taking up 4 or less star fights, that combination is beyond useless. You might as well forfeit, if that was possible.
Take note that BFs and derivations are usually the hardest because of no itens at all to use.