The Rényi $α$-entropy $H_α$ of complete antisymmetric directed graphs (i.e., tournaments) is explored. We optimize $H_α$ when $α= 2$ and $3$, and find that as $α$ increases $H_α$'s sensitivity to what we refer to as `regularity' increases as well. A regular tournament on $n$ vertices is one with each vertex having out-degree $\frac{n-1}{2}$, but there is a lot of diversity in terms of structure among the regular tournaments; for example, a regular tournament may be such that each vertex's out-set induces a regular tournament (a doubly-regular tournament) or a transitive tournament (a rotational tournament). As $α$ increases, on the set of regular tournaments, $H_α$ has maximum value on doubly regular tournaments and minimum value on rotational tournaments. The more `regular', the higher the entropy. We show, however, that $H_2$ and $H_3$ are maximized, among all tournaments on any number of vertices by any regular tournament. We also provide a calculation that is equivalent to the von Neumann entropy, but may be applied to any directed or undirected graph and shows that the von Neumann entropy is a measure of how quickly a random walk on the graph or directed graph settles.