Problems with solutions represented by permutations are very prominent in combinatorial optimization. Thus, in recent decades, a number of evolutionary algorithms have been proposed to solve them, and among them, those based on probability models have received much attention. In that sense, most efforts have focused on introducing algorithms that are suited for solving ordering/ranking nature problems. However, when it comes to proposing probability-based evolutionary algorithms for assignment problems, the works have not gone beyond proposing simple and in most cases univariate models. In this paper, we explore the use of Doubly Stochastic Matrices (DSM) for optimizing matching and assignment nature permutation problems. To that end, we explore some learning and sampling methods to efficiently incorporate DSMs within the picture of evolutionary algorithms. Specifically, we adopt the framework of estimation of distribution algorithms and compare DSMs to some existing proposals for permutation problems. Conducted preliminary experiments on instances of the quadratic assignment problem validate this line of research and show that DSMs may obtain very competitive results, while computational cost issues still need to be further investigated.