In this article, we have thoroughly studied the electronic structure and 4f-ligand covalency of six mononuclear dysprosium organometallic sandwich complexes [Dy(CmRm)2]n+/- (where R = H, SiH3, CH3; m = 4 to 9; n = 1, 3) using both the scalar relativistic density functional and complete active space self-consistent field (CASSCF) and N-electron valence perturbation theory (NEVPT2) method to shed light on the ligand field effects in fine-tuning the magnetic anisotropy of these complexes. Energy decomposition analysis (EDA) and ab initio-based ligand field theory AILFT calculations predict the sizable 4f-ligand covalency in all these complexes. The analysis of CASSCF/NEVPT2 computed spin-Hamiltonian (SH) parameters indicates the stabilization of mJ |±15/2〉 for [Dy(C4(SiH3)4)2]- (1), [Dy(C5(CH3)5)2]+ (2) and [Dy(C6H6)2]3+ (3) complexes with the Ucal value of 1867.5, 1621.5 and 1070.8 cm-1, respectively. On the other hand, we observed mJ |±9/2〉 as the ground state for [Dy(C7H7)2]3- (4) and [Dy(C8H8)2]- (5) complexes with significantly smaller Ucal values of 237.1 and 38.6 cm-1 respectively. For the nine-membered ring [Dy(C9H9)2]+ (6) complex, we observed the stabilization of the mJ |±1/2〉 ground state, with the first excited state being located ∼29 cm-1 higher in energy. AILFT-NEVPT2 ligand field splitting analysis indicates that the presence of π-type 4f-ligand interactions in complexes 1-3 help generate the axial-ligand field, while the δ-type interactions in complexes 4-5 generate the equatorial ligand field despite the ligands approaching from the axial direction. As the ring size increases, φ-type interactions dominate, generating a pure equatorial ligand field stabilising mJ |±1/2〉 as the ground state for 6. Calculations suggest that the nature of the ligand field mainly governs the Ucal values in the following order: 4f-Lσ > 4f-Lπ > 4f-Lδ > 4f-Lφ. Calculations were performed by replacing ligands with CHELPG charges to access the crystal field (CF) effects which suggests the stabilization of pure mJ |±15/2〉 in all the charge-embedded models (1Q-6Q). Our findings point out that the crystal field and ligand field effects complement each other and generate a giant barrier for magnetic relaxation in the small ring complexes 1-3, while a relatively weak crystal field and adverse 4f-Lδ/4f-Lφ interactions diminish the SMM behaviour in the large ring complexes 4-6.