For those wondering why the Guild Master gave him the "win" so easily?
Keep in mind she's a former S-Rank, and it's been implied that she was one of the strongest out of all the S-Ranks. He's only testing for A-Rank here. So if she is that powerful? Then it makes sense that, "It is enough for you to merely score a hit on me."
In a ways, it's a bit like in Naruto with Kakashi's Bell Test - it wasn't about getting the bells. It was about working together as a proper cell. Similar case here: it's not about beating her. It's whether or not he could land a single hit on her. And her being the Guild Master and the proctor for the test? No one can say a damn thing about it if she says, "Yep, that was gonna hit. No need for me to get hurt - I got things to do, you know."