Middray/Chronology

The Octagram Soars Brightly Arc
Middray is introduced alongside Hermes as both attempt to persuade Yamza, to have his army refrain from depleting more of their resources, reaching the limit of what they could provide. Yamza coldly rejects their plea and brings up that he's here to clean up the mess Milim made of Kleiman's plans, and since he's provided a written edict from Milim herself, granting passage through her territory among other rights, the Dragon Faithful should cooperate with him to the best of their abilities. Middray begrudgingly accepts. Yamza then orders them to prepare troops for him, but Hermes let out a complaint to that, in which Yamza reacts by lopping his arm off. Before things could escalate, Middray sends Hermes flying to a nearby wall and apologizes to Yamza for Hermes' disrespect, and asks to let him handle his punishment. Yamza reluctantly leaves, successfully resolving the situation.

After getting a room to themselves, Middray releases his bottled anger as he heals Hermes' arm, spitting curses at Yamza for injuring a servant of Milim, to which Hermes retorts in his head that Middray is also guilty of the same crime. Following that, they're seen on the battlefield providing logistical support to Kleiman's army. As they witness Yamza's force suffering significant losses to Rimuru's army, Gabiru and Suphia approach them. Following a few exchanges, they introduce themselves and state their affiliation with Milim, with the battle after that devolving to a sparring session on Middray's insistence. They continue going at it for a while but halted once they sensed Charybdis in the distance. They readied themselves to defend but not too soon was the threat swiftly dispatched by Benimaru. The next moment, Benimaru teleports in on them and notices the friendly atmosphere. After a few talks, the battle is officially over.