In this paper I want to propose a theoretical comparison between Kant's transcendental philosophy and Hegel's speculative one, and I argue that both - according to their peculiar method - determine an epistemological grounding of metaphysics. The foundations converge for what concerns the need of a scientific self-founded knowledge, which is universally valid and actually necessary, without occurring to arbitrary and extrinsic assumptions. Nevertheless, they differ as of the foundational technique, the overall epistemology and its metaphysical outcome. Indeed, while Kant's foundational criteria is given by the transcendental deduction, Hegel's is made up of the dialectic. Furthermore, while Kant's transcendental philosophy determines a metaphysica generalis, by means of a linear, vertical epistemology which has a twofold ontological foundation, conversely Hegel's speculative philosophy, by virtue of an epistemology which consists of a single circle of scientific knowledge, and which foundation is "broken at the bottom" (abgrundiger Grund), also determines a metaphysica specialis.