As per the five-year provincial roads plan (2017 edition), the Department of Transportation and Works of Government of Newfoundland and Labrador shifted its focus from the construction of new roads to the maintenance and rehabilitation of existing highways. With more than 270 km of road planned to be rehabilitated/upgraded in the province by 2022, appropriate strategies are needed to maintain and rehabilitate the roads. Many past studies reported that the life of overlays depends on the interface condition between the existing pavement and overlay. In addition to this, the overlay fails mainly due to lack of proper maintenance for existing pavement before constructing the overlay. In this paper, Finite Element-based software program (ABAQUS) was employed to evaluate the interlayer damages between the existing pavement and overlay. Various interface conditions are modelled for evaluating the performance of the overlay. The results obtained from the analysis could help in selecting appropriate maintenance strategies for developing a sustainable overlay construction specification.