Middray/Chronology

The Octagram Soars Brightly Arc
Middray is introduced alongside Hermes, pleading with Yamza to have his army refrain from depleting the resources of the Dragon Faithful any further than they already have as they've reached the limit of what they could provide. Yamza coldly rejects and brings up that he came to them to clean up the mess Milim made of Clayman'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 and has his arm lopped off. Before things could escalate, Middray sends Hermes flying to a nearby wall with a heavy kick and apologizes to Yamza for Hermes' disrespect, asking to let him handle his punishment. Yamza reluctantly accepts and leaves, successfully resolving the situation.

After getting a room to themselves, Middray releases his bottled anger as he heals Hermes' arm, and spits 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 Clayman's army. As they witness Yamza's force suffering staggering losses to Rimuru's army, Gabiru and Suphia approach them. After a few exchanges, Middray and Hermes introduce themselves and state their affiliation with Milim, after which the battle devolves to a sparring session on Middray's insistence. They go 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.