This study presents a numerical investigation into the adhesion strength of micro fibrillar structures, incorporating statistical analysis and the effects of excessive pre–load leading to fibril buckling. Fibrils are modeled as soft cylinders using the Euler–Bernoulli beam theory, with buckling conditions described across three distinct states, each affecting the adhesive properties of the fibrils. Iterative simulations analyze how adhesion strength varies with pre–load, roughness, number of fibrils, and the work of adhesion. Roughness is modeled both in fibril heights and in the texture of a rigid counter surface, following a normal distribution with a single variance parameter. Results indicate that roughness and pre–load significantly influence adhesion strength, with excessive pre–load causing substantial buckling and a dramatic reduction in adhesion. This study also finds that adhesion strength decreases exponentially with increasing roughness, in line with theoretical expectations. The findings highlight the importance of buckling and roughness parameters in determining adhesion strength. This study offers valuable insights into the complex adhesive interactions of fibrillar structures, offering a scalable solution for rapid assessment of adhesion in various rough surface and loading scenarios.