Traditional water-based dyeing of polyester textiles usually generates burdensome processes and a great deal of wastewater, which can no longer meet the green and sustainable developments in the textile dyeing industry. In the silicone waterless dyeing system, polyester textiles can be dyed with disperse dye without water. However, the dyeing performance of polyester textiles is influenced by the dispersant. In this study, the relationship between the properties of dispersants and disperse dyeing performance was studied. When the amount of dispersant NNO (2-Naphthalenesulfonic acid) was 1.2%, the exhaustion of disperse red 177 and the final K/S value of the dyed fabric improved to 94.18% and 14.73, respectively. However, the exhaustion of disperse red 177 was reduced from 90.73% to 82.61%, and the final K/S value of the dyed fabric was decreased from 14.77 to 14.01 when the dosage of MF (Naphthalenesulfonic acid) was 1.2%. Compared with different dyeing systems, the final uptake of disperse red 177 was 93.81% and 94.18% in traditional water-based and silicone waterless dyeing systems and the K/S value of the dyed fabric was almost the same. The washing and rubbing fastness (wet and dry) of the dyed fabric were found to be at a level of 4 or 4–5, and the light fastness of the dyed fabric was 3–4. If only the dispersant was added in the silicone waterless dyeing system, there was no leveling problems on dyed samples. Moreover, the maximum absorption wavelength of disperse red 177 was not changed after adding the dispersant. With an increasing amount of dispersant NNO, the solubility of the dye in the silicone solvent decreased, but it increased with an increasing amount of dispersant MF. In the relationship between dye exhaustion and dye solubility in a silicone waterless dyeing system, the exhaustion of dye was linearly and inversely proportional to the dye solubility. A dispersant with better hydrophilicity can decrease the solubility of the dye in dyeing media, and the dyeing performance of dye is better. Compared with previous studies, the exhaustion of dye was consistent with the ClogP value (hydrophobic constant) of the dyeing accelerant. Therefore, a dispersant with high hydrophilicity can reduce the solubility of dye and improve the exhaustion of disperse dye in a silicone waterless dyeing system. Moreover, the color fastness of the dyed fabric did not change before and after adding the dispersant.