Elf (Wing) & Orc (Krag)

Here, the elf is almost done for, especially with a well-built Orc. ~ -40% initiative from artifacts (if there are no items with +initiative), and if it's combined with Command Aura + Education + Defense, it's guaranteed. Even with just a Ring of Cold + Azure Dagger + Rain of Arrows + Cursed + Enchanted Arrow + Deadly Cold + Amulet of Cold + Lord of Cold... it's still unlikely. He needs Offensive Unit and Darkness... at that stage, he could even learn all the Darkness spells. Since there's a mentor, he'll level up in Command Aura. He'll eliminate the ranged units, then he can switch Cold to Meteor Shower, and the amulet to green boots... Although, the freezing effect won't be noticeable, even though the ring doesn't provide much of it. You could also try Lord of Fire + Fireball. You can significantly reduce the Orc's defense. But -40% initiative is a lot! And if there's a Chaos Shield...

Honestly, the chances are small if the Orc levels up correctly and has a lot of hit points.