This paper is concerned with a boundary-value problem on the half-line for nonlinear two-dimensional delay differential systems with positive delays. A theorem is established, which provides sufficient conditions for the existence of positive solutions. The application of this theorem to the special case of second-order nonlinear delay differential equations is given. Also, the application of the theorem to two-dimensional Emden–Fowler-type delay differential systems with constant delays is presented. Moreover, some general examples demonstrating the applicability of the theorem are included.