Explain this madness

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I think those things are supposed to be arrows:)

You are completely right! you must be smart

I've studied arrow signs for years. Sometimes they can confuse people when they just pop up out of nowhere;)

This should help OP..... 

how should it help?

I'm going to need more direction to solve this problem for you.  Explain further.

I win against everyone except the lowest rated player of these 5

It's probably because sometimes we play better, sometimes worse than our ratings would suggest.  Probably because we are human.

Having a rating 280 Elo larger than your opponent only means you will score 84% against him. Not that you always win, and not that there can be no losses amongst the non-wins.

In practice Chess is a game of chance, as you will have to take decisions you cannot fully foresee the consequences of.