The inclusion process of clomiphene into β-cyclodextrin was investigated using various molecular modelling techniques, including static quantum computational (QC) methods, molecular dynamics (MD) and sequential QC/MD approaches. The calculated association constant (KexptEZ=46.94×M−1) showed good agreement with the experimental data (KexptEZ=50.21×M−1), reflecting contributions from both multi-equilibrium processes and the fixed composition of the isomeric mixture. These results enhance understanding of the inclusion process and propose new methodological approaches for future research. (Image credit: Hélio F. Dos Santos.)