Syn Dihydroxylation of Alkenes The answer makes sense to me. However, what if $\ce{OsO4}$ were to attack from the other side of the double bond? Why does the answer key not show that possibility? Would we not get an other molecule?
If you look carefully you'll see that your compound has stereocenters, yet is achiral.  Both stereocenters have the opposite configuration.  This is the meso-form, these are achiral, and the hydroxy groups are prochiral.  Look carefully for the rotoinversion center!