Any semigroup $\mathcal{S}$ of stochastic matrices induces a semigroup majorization relation $\prec^{\mathcal{S}}$ on the set $Δ_{n-1}$ of probability $n$-vectors. Pick $X,Y$ at random in $Δ_{n-1}$: what is the probability that $X$ and $Y$ are comparable under $\prec^{\mathcal{S}}$? We review recent asymptotic ($n\to\infty$) results and conjectures in the case of majorization relation (when $\mathcal{S}$ is the set of doubly stochastic matrices), discuss natural generalisations, and prove a new asymptotic result in the case of majorization, and new exact finite-$n$ formulae in the case of UT-majorization relation, i.e. when $\mathcal{S}$ is the set of upper-triangular stochastic matrices.