In order to satisfactorily discharge a financial obligation, Islamic finance prescribes similar for similar or equal for equal (mithliy bi mithliy), unless where similar becomes impossible or unobtainable, then the resort is made to worth or value (qīmah). However, opinions of the jurists differ as to determination, identification or verification precisely of what is mithliy, which may affect the actualisation of debt settlement and make it ambiguous. In this situation, the substitution of qīmiy for mithliy becomes inevitable. In doing so, fear of falling into riba or causing injury to either debtor or creditor arises, particularly where rebatable (usurious) items such as gold and silver (dhahb wa fiḍḍah), currencies (nuqūd), animal (ḥayawān) are involved. This paper, therefore, studied scholarly opinions about the identification of “similar items” (mithliyāt) and “valued items” (muqawwamāt). It used primary and secondary sources of Sharīʻah. Fiqh manuals, books of tafsīr, ḥadīth and relevant periodicals and articles were consulted. The study revealed that parties face difficulties in actualising similarity while settling financial obligations. Therefore, the paper suggested the inclusion of a “statement of similar or worth property” while making a financial agreement.