DFT results for these systems fall into two categories. In one category are complexes 4a, 7b, and ellipticine@DNA, for which many of the DFT values lie between the two reference energies so there can be no consensus as to the sign of the DFT errors. On the other hand, for 2a, 2b, 5a, and 6a the DFT results are mostly characterized by systematic overbinding as compared to either benchmark, by up to 6.6 kcal/mol (BLYP+D3) for 2a, 4.9 kcal/mol (ωB97X-D) for 2b, or 8.3 kcal/mol (B97+D3) for 6a. [Quoted numerical errors reflect the DLPNO-CCSD(T 0 )/ CBS reference value.] The M06-2X functional, however, consistently performs very well and is within about 1 kcal/mol of DLPNO-CCSD(T 0 )/CBS for all four of these complexes, although it performs poorly for 4a (error = 14.1 kcal/mol) and 7b (error = 7.4 kcal/mol). All functionals overbind the amide macrocycle complex 5a, 316 by at least 3.5 kcal/mol with respect to the DLPNO-CCSD(T 0 )/CBS reference. The indinavir@HIV complex is the largest system examined herein, with a benchmark E int = -121.50 kcal/mol computed at the DLPNO-CCSD(T 0 )/CBS level. Some functionals come close to this although results overall are varied, with errors as large as 15 kcal/mol for M06-2X and 27 kcal/mol for B97+MBD.