For convenience we'll work in the hyperbolic upper half plane $H$. We are given a hyperbolic quadrilateral $Q$ with vertices $a,b,c,d$ and geodesic segment edges $[ a,b ]$ $[ b,c ]$ $[ c,d ]$ $[ d,a ]$. We are also given that $\angle abc=\angle bad=\frac{\pi}{2}$ and $\rho_H([a,d])=\rho_H([b,c])$ where $\rho_H([x,y])$ is the hyperbolic length of the geodesic segment from $x$ to $y$. Can we conclude that $\rho_H([a,b])<\rho_H([c,d])$?
It's clear that by a transformation by an isometry, we can put the segment $[a,b]$ on the imaginary axis and then the segments $[a,d]$ and $[b,c]$ will be segments of half circles with centre at $0$ and of equal length, so the points $c$ and $d$ lie on the same 'ray' extending from the origin. This clearly implies that $\alpha=\angle bcd=\angle cda$ and, by the Gauss-Bonnet Theorem, we may also deduce that $0<Area_H(Q)=2\pi-(\frac{pi}{2}+\frac{pi}{2}+\alpha+\alpha)$ and so conclude that $\alpha<\frac{\pi}{2}$ (although this can be fairly easily seen graphically).
I feel like the proof that $\rho_H([a,b])<\rho_H([c,d])$ should be obvious and hinges on the fact that $0<\alpha<\frac{\pi}{2}$, but playing around with hyperbolic trigonometric identities has just led to a rather large mess.
I should point out that this was the beginning of an attempt to prove something which I have now proved using a different method. I am, however, curious to see if this method would have worked.