What is your friends armour?
Let's assume he has maximum armour for a warrior, which is 50%. Then the damage you can do to him would not be 1100014000, but 65007000.
Likewise, with your 22% of armour his damage range would change from 55007800. So your damage ranges overlap more than you think.
In an actual fight, it's a little more complicated as not all precise factors are known, so those numbers are very rough estimates.
Another thought: Does he use potions (or did he in the fight you mentioned?)? This can greatly effect damage when he uses (a) strength potions (increasing his own damage) or (b) dexterity potions (lowering your damage).
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