Background In the management of mallet deformities, oblique retinacular ligament (ORL) reconstruction provides a mechanism for automatic distal interphalangeal (DIP) joint extension upon active proximal interphalangeal joint extension. The two variants of ORL reconstruction utilize either the lateral band or a free tendon graft. This study aims to compare these two surgical techniques and to assess any differences in functional outcome. As a secondary measure, the Mitek bone anchor and pull-in suture methods are compared. Methods A single-institutional retrospective review of ORL reconstruction was performed. The standard patient demographics, injury mechanism, type of ORL reconstruction, and pre/postoperative degree of extension lag were collected for the 27 cases identified. The cases were divided into lateral band (group A, n=15) and free tendon graft groups (group B, n=12). Group B was subdivided into the pull-in suture technique (B-I) and the Mitek bone anchor method (B-II). Results Overall, ORL reconstructions had improved the mean DIP extension lag by 10° (P=0.027). Neither the reconstructive technique choice nor bone fixation method identified any statistically meaningful difference in functional outcome (P=0.51 and P=0.83, respectively). Soft-tissue injury was associated with 30.8° of improvement in the extension lag. The most common complications were tendon adhesion and rupture. Conclusions The choice of the ORL reconstructive technique or the bone anchor method did not influence the primary functional outcome of extension lag in this study. Both lateral band and free tendon graft ORL reconstructions are valid treatment methods in the management of chronic mallet deformity.