Within ecclesiastical circles, both from the perspective of legal practice and ordinary relational matters between ecclesiastical entities, the theme of contract very scarcely occupies a place of prominence. It is a situation that is due on the one hand, and to a large extent, to the fact that the canonisation of civil law on contracts (c. 1290 CIC/1983) has had the consequence of transferring the preoccupation of the entities on this matter to the domain of civil law. Besides, and still connected to the above, is the tendency to attribute a merely pastoral relevance to their relationships, with little or no reference to the juridic aspects inherent in these relationships. It is a situation that is largely responsible for the crisis which do not uncommonly characterise some of these relationships as verified over the centuries; particularly in the relationship between dioceses and religious institutes. The issuance of various papal and conciliar exhortations before and after Vatican II, as well as the normative instructions and legal provisions contained in various juridic documents, most prominently cc. 271, 520, 681 and 790 of CIC/1983, has gone a long way to dissipate some of the tensions of the past. However, the true nature of how the contractual relationship between ecclesiastical entities, including the attendant issues of conceptual understanding, civil status of ecclesiastical entities, resolution of contractual disputes, etc., remains a matter of investigative interest for the canonist. This is, in a nutshell, the substance of this research work. The conclusions arrived at offer the reader an insight into the available untapped resources within the ecclesiastical legal system, as well as some considerable possibilities which remain to be explored to the benefit of the subjects of canon law.