one easy reason he beat you, his shout.
-100 damage from your attacks, means you hit for zero damage on him, and in ult mode he gets full fury bar, which means max crit, with a few crit runes, and masteries that is nearly 80% crit chance with almost no gear, so even with 100 damage he going to smack you for 200 a hit.
Meanwhile you have -100 damage applied to you for the fight.
people forget melee can't beat tryn 1vs1 cause of his shout, its not just a slow, it's an ad debuff and a super OP one at that.
oh and next time save your ult till after you wear him down, that way when he ults you ult, blocks his insane damage, and gives him only 1 second to cast his heal to save self, which means he no longer has fury thus no damage.
Which means he will spin off hoping to live.
Wnat to fix tryn's kit, mocking shout takes a AD reduction nerf to - 50 instead of -100.
And he can no longer spin through walls. Poof tryn no longer OP but still just as strong.