Zeref Dragneel vs. Ultear Milkovich

Zeref vs. Ultear Milkovich is a battle fought between the Black Mage, Zeref, and the eldest of the Seven Kin of Purgatory from Grimoire Heart, Ultear.

Prologue
Ultear is walking in the forest of Tenrou island, saying that the path of Zeref was too much for her, but today her dream will finally come true and once she has Zeref on her hands, she will be saved. As she is talking, someone comes out of the bushes and asks her if she was looking for him. Ultear is surprised to see him and he tells Ultear that they are an "apple of discord", and that it's sad how they've managed to anger him, Zeref.

When Ultear sees who it is, tears come out of her eyes. She thinks to herself that after searching for him for so long, Zeref is finally right before her eyes. Zeref asks her if what she wants is his power, Ultear kneels before him and responds that what she wants is his entire existence and calls him Lord. Zeref says that he has no intention of doing anything in this period, he doesn't want to see wars or people dying and tells Ultear to stop attacking the island and leave at once. He repeats that he is angry, emitting a dark aura and causing Ultear to start shaking in fear.

Battle
The details of this battle are unknown.

Aftermath
Ultear is standing over Zeref, who is on the ground, gasping for air. She tells him that he may be a legendary Mage, but in his sleeping state he is nothing. She screams to him not to underestimate the eldest of the Seven Kin of Purgatory. Zeref tries to move, but fails and Ultear says that it is since they have the key that will wake him up. Zeref tells her to stop, she ignores him and screams loudly that she has Zeref.