A proper benchmarking on the properties of HF and its dimer inside C60 using density functional theory (DFT) based approaches is presented. For this purpose, 10 different DFT functionals following Jacob’s Ladder have been chosen. Geometrical parameters, viz., bond length, bond angle, etc., and dipole moment have been computed. Two types of orientations, viz., L-shaped and anti-parallel of (HF)2 inside C60 are considered, the latter with an extremely short hydrogen bond. HF bond lengths are elongated upon encapsulation in comparison to its free state analogue. The calculated stability of HF@C60 is functional dependent whereas, (HF)2C60 is thermodynamically unstable for all the functionals. The kinetic stability of (HF)2@C60 is observed through ADMP simulation at 300K temperature. The red shift in HF stretching frequencies is noticed in all cases. NCI analysis exhibits a non-covalent type interaction between HF dimer and the C60 cage. The total interaction energy is found to be negative for HF@C60. EDA analysis showed a high value of repulsive ΔEpauli which makes the (HF)2@C60 system unstable except for the functional BP86-D3 of GGA family. Furthermore, QTAIM analysis is performed and confirmed the presence of (3, -1) bond critical point along the hydrogen bond region for L-shaped (HF)2C60.