The treatment of the concepts of entitlement and delimitation in the case law, and their relationship, has often lacked clarity. While seeking for equitable outcomes that consider the specificities of each case, international courts and tribunals have at times failed to approach these two concepts in a consistent manner. From the perspective of legal argumentation and discourse, a clear conceptual construction of maritime delimitation law has remained unattained. This ultimately resulted in uncertainty and unpredictability in judicial and arbitral decision-making, in the doldrums of which one continues to subsist. This chapter looks into several aspects concerning entitlement and delimitation, and the relationship between the two, within the three-stage process. Predicated on a critical review of the case law, it attempts to canvass certain conceptual features of maritime delimitation law, including: the land dominates the sea; principle of maritime zoning; basis of entitlement; provisional equidistance line; and adjustments to the provisional line. The conclusion is that ‘bridging the gap’ between the relevant circumstances and the adjudged boundary-line through proper judicial argumentation and discourse is pivotal not only to shed light on the relationship between entitlement and delimitation, but also to reach equitable solutions that are sounder in the eyes of delimitation law.