The trouble is in ambiguity. Notation $\cdot ^{-1}$ can mean both inverse and preimage, when it comes to functions. Also note that if $f\colon X\to Y$, $f^{-1}$ can denote a function $f^{-1} \colon \mathcal P(Y)\to\mathcal P(X)$ that assigns to each subset of $Y$ its preimage under $f$. Thus, $(f^{-1})^{-1}$ could be four different things:
1) Inverse of inverse:
In this case $(f^{-1})^{-1} = f$ by uniqueness of inverse. Thus, $(f^{-1})^{-1}(A) = f(A)$.
2) Preimage of inverse:
In this case, since $f$ is invertible, the preimage is just the image of $f$. Thus, $(f^{-1})^{-1}(A) = f(A)$.
3) Inverse of the above preimage function.
We will inspect this shortly.
4) Preimage of the above preimage function:
This, I think, would just be strange, unless this comes from some set theory course, and in this case $(f^{-1})^{-1}(A) = f(A)$ wouldn't even make sense since $A$ would need to be subset of $\mathcal P(X)$ and not subset of $X$ which is required for $f(A)$ to make sense.
The only interesting case is 3), and let us prove two things:
a) $f^{-1}$ is injective $\implies$ $f$ is surjective
b) $f^{-1}$ is surjective $\implies$ $f$ is injective
Assume the $f$ is not surjective. Then, $f^{-1}(f(X)) = X = f^{-1}(Y)$, but $f(X)\neq Y$, so $f^{-1}$ is not injective. This proves a) by contraposition.
Now, assume that $f^{-1}$ is surjective and let $x_1, x_2\in X$ such that $f(x_1) = f(x_2)$. Since $f^{-1}$ is surjective, there is an $A\subseteq Y$ such that $f^{-1}(A) = \{x_1\}$. Obviously, $f(x_2) = f(x_1)\in A$, by definition, but then $x_2\in f^{-1}(A) = \{ x_1\}$, and thus $x_1 = x_2$, so $f$ is injective.
Combining a) and b), we have that if the preimage $f^{-1}$ is bijective, so is $f$. We then claim that the inverse of the preimage $f^{-1}$ is just the image of $f$. But this is obvious since for invertible $f$ we have that $f(f^{-1}(A)) = A$ and $f^{-1}(f(A)) = A$.
Thus, in case 3), again we have $(f^{-1})^{-1}(A) = f(A)$.
In conclusion, $(f^{-1})^{-1}(A) = f(A)$ makes sense if and only if $f$ is invertible, and in all meaningful interpretations is true.