Searching for Higgs bosons beyond the Standard Model (BSM) is one of the most important missions for hadron colliders. As a landmark of BSM physics, the MSSM Higgs sector at the LHC is expected to be tested up to the scale of the decoupling limit of O(1) TeV, except for a wedge region centered around tan β ∼ 3 − 10, which has been known to be difficult to probe. In this article, we present a dedicated study testing the decoupled MSSM Higgs sector, at the LHC and a next-generation pp-collider, proposing to search in channels with associated Higgs productions, with the neutral and charged Higgs further decaying into tt and tb, respectively. In the case of neutral Higgs we are able to probe for the so far uncovered wedge region via pp → bbH/A → bbtt. Additionally, we cover the the high tan β range with pp → bbH/A → bbτ τ . The combination of these searches with channels dedicated to the low tan β region, such as pp → H/A → tt and pp → ttH/A → tttt potentially covers the full tan β range. The search for charged Higgs has a slightly smaller sensitivity for the moderate tan β region, but additionally probes for the higher and lower tan β regions with even greater sensitivity, via pp → tbH ± → tbtb. While the LHC will be able to probe the whole tan β range for Higgs masses of O(1) TeV by combining these channels, we show that a future 100 TeV pp-collider has a potential to push the sensitivity reach up to ∼ O(10) TeV. In order to deal with the novel kinematics of top quarks produced by heavy Higgs decays, the multivariate Boosted Decision Tree (BDT) method is applied in our collider analyses. The BDT-based tagging efficiencies of both hadronic and leptonic top-jets, and their mutual fake rates as well as the faking rates by other jets (h, Z, W , b, etc.) are also presented.