IRON LEDGEROPPONENT CASE FILE
Ultear Milkovich fought Zeref and Gray from chapter 221 to chapter 241. Chapter 221 (episode 106): Zeref lost to Ultear Milkovich. Chapter 241 (episode 116): Gray beat Ultear Milkovich.
Encountered in the forests of Tenrou Island, a dormant Zeref is unable to control his Black Magic; Ultear uses Arc of Time to manipulate surroundings and knocks Zeref down with Luminous Minutes.
Files L because Zeref is overpowered and captured while in his dormant sleeping state.
Gray Fullbuster fights Ultear Milkovich through a prolonged magical contest and survives her final assault. His counterattack leaves Ultear defeated and unable to continue.
A ruling treats the long transformation-heavy encounter as one event and uses the chapter where the result resolves.