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I know that it is the case for when $\sup A < \sup B$, because it implies that set $A$ is bounded above and the elements of $B$ are greater than $A$. Would it be because set $A$ could be the same as set $B$ or at least have the same supremum?

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What if $A=B=(0,1)$?${}{}{}{}{}{}{}{}{}{}{}{}{}{}{}{}{}{}{}{}$

I think your intuition is correct. If $\sup A\leq\sup B$, but strict inequality doesn't hold, then equality certainly holds.