Doom Curse didn't work as it's suppose to

Me and opponent both had one prize left. I use Hisuian Zoroark's Doom Curse on him, he use Bosses Orders to make me switch to the bench, (which DOESN'T stop Doom Curse,) and knock out my Pokemon and then Doom Curse didn't go off at all… he should have been knocked out and then it would've been Sudden Death… but the game cheats against me, ALL OF THE TIME.