Dylan looked at Deamon in absolute surprise. When it came to fights, even back then at the Orphanage, he was naturally stronger because of his S-Grade dantain.
And Although he was not one that absolutely enjoyed violence, it was just one of those things that could not be peeled from the kids of the street, hence you would have someone step on you.
He was not one to allow another person step on him. Hence, his prowess.
On the Other hand, Deamon was not the kind to actively engage in conflict, and that was not because he did not want to, but because he was usually the weaker party.
Now that Dylan thought about it, he should have suspected something when Deamon agreed to battle him. After all, Deamon was such a man to not pick fights that he was not sure that he would win.