Triplet energy transfer (TET) from semiconductor quantum dots (QDs) is an emerging strategy for sensitizing molecular triplets that have great potential in many applications. Here, CdSe QDs with varying sizes and 1-pyrenecarboxylic acid (PCA) are selected as the triplet donor and acceptor, respectively, to study the TET and charge transfer dynamics as well as enhanced singlet oxygen (1O2) generation properties. The results from static and transient spectroscopy measurements demonstrate that both the TET and hole transfer occur at the QDs-PCA interface. The observed significant drop in TET efficiency from 52 to 8% with increasing QD size results from the reduced TET driving force between the QDs and PCA, which is further confirmed by the more efficient sensitization of the anthracene derivative with a large TET driving force. In contrast, the hole transfer efficiency displays a small decrease with an increasing QD size due to a slight change in the hole driving force. The sensitized PCA triplets show a good ability of 1O2 generation, and the 1O2 formation rate increases 10-fold as the QD size decreases from 3.3 to 2.4 nm. These findings provide a profound understanding of the TET and hole transfer mechanism from QDs to molecules and are significant in designing efficient 1O2 generation systems based on semiconductor QDs and triplet molecules.