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I think the cat should have said something about the upgrades.

I beat the boss with no upgrades since I didn't realize you could dash over the green slime. 

Then the upgrades made the endurance match into a joke.

You beat it without collecting the items? I thought I made it impossible. Also, the cat is not to be trusted.

Hey, my bullets did damage, so I knew I could win. It took like 5-10 minutes, but I got it!

The key is to just camp at one part of the arena and randomly fire shots out. If they don't hit, oh well, you'll get it eventually.