We comprehensively study the charged-Higgs contributions to the leptonic B − q → ℓν (q = u, c) and semileptonicB → X q ℓν (X u = π, ρ; X c = D, D * ) decays in the type-III two-Higgs-doublet model (2HDM). We employ the Cheng-Sher ansatz to suppress the tree-level flavor-changing neutral currents (FCNCs) in the quark sector. When the strict constraints from the ∆B = 2, b → sγ, and pp(bb) → H/A → τ + τ − processes are considered, parameters χ u tq from the quark couplings and χ ℓ ℓ from the lepton couplings dictate the leptonic and semileptonic B decays. It is found that when the measured B − u → τν and indirect bound of B − c → τν obtained by LEP1 data are taken into account, R(D) and R(π) can have broadly allowed ranges; however, the values of R(ρ) and R(D * ) are limited to approximately the standard model (SM) results. We also find that the same behaviors also occur in the τ -lepton polarizations and forward-backward asymmetries (A Xq,τ F B ) of the semileptonic decays, with the exception of A D * ,τ F B , for which the deviation from the SM due to the charged-Higgs effect is still sizable. In addition, the q 2 -dependent A π,τ F B and A D,τ F B can be very sensitive to the charged-Higgs effects and have completely different shapes from the SM.LHCb reported more than a 2σ deviation from the SM in R(K) = BR(B + → K + µ + µ − )/BR(B + → K + e + e − ) = 0.745 +0.090 −0.074 ± 0.036 [84] and R(K * ) = BR(B 0 → K * 0 µ + µ − )/BR(B 0 → K * 0 e + e − ) = 0.69 +0.11 −0.07 ± 0.05 [85]. Since we concentrate on the treelevel leptonic and semileptonic B decays, we do not address this issue in this work. The charged-Higgs contributions to the b → sℓ + ℓ − processes can be found in [86][87][88][89][90][91].The paper is organized as follows: In Section II, we discuss and parametrize the charged-Higgs Yukawa couplings to the quarks and leptons in the type-III 2HDM. In Section III, we study the charged-Higgs contributions to the leptonic B − u(c) → ℓν andB → (P, V )ℓν decays, where the interesting potential observables include the decay rate, the branching fraction ratio, lepton helicity asymmetry, and lepton forward-backward asymmetry. We study the tree-and loop-induced ∆B = 2 and loop-induced b → sγ processes in Section IV, where the contributions of neutral scalar H, neutral pseudoscalar A, and charged-Higgs are taken into account. The detailed numerical analysis and the current experimental bounds are shown in Section V, and a conclusion is given in Section VI.