Kikansha no Mahou wa Tokubetsu desu 2nd Season

Desir Arman returned 13 years into the past after witnessing the world end inside the Shadow Labyrinth, determined to use his second chance to prevent that disaster. After his time at Hebrion Academy, he no longer fights alone. Romantica, Pram, and Azest now stand beside him, people whose future losses Desir understands better than they ever could.

When another Shadow World appears, danger begins resembling the memories he has tried to outrun. Desir is haunted by a vision of Romantica's death, and a name tied to the tragedy of his previous life emerges again: Dadaneuph, the Demon of Destruction. His calculations begin anew, but this time he must save his companions before the past becomes the future whose ending he already knows.