The spatial distribution and chiral signatures of organochlorine pesticides (OCPs) in the surface sediments of Xinghua Bay, southern East China Sea, were investigated. The total OCP concentrations ranged from 9.15 to 40.5 ng/g dry weight, with a predominance of hexachlorocyclohexanes (HCHs) and dichlorodiphenyltrichloroethanes (DDTs). The isomer ratios of α-HCH/γ-HCH (less than 1.0) and the predominant β-HCH implied that HCH residues were derived not only from historical technical HCH use but also from the additional use of lindane in this area. The isomer ratios of p,p′-DDT/(p,p′-DDD + p,p′-DDE) and o,p′-DDT/p,p′′-DDT, and a strong correlation (R = 0.83, P < 0.001) between p,p′-DDE and o,p′-DDT depicted a cocktail input pattern of dicofol-type DDT and technical DDT. Moreover, the fact that only cis-chlordane was detectable for all sampling stations suggested the past application of technical chlordane. Based on the sediment quality guidelines (SQG), γ-HCH is the main OCP species of ecotoxicological concern in Xinghua Bay. Enantiomeric analysis showed that the (+)-enantiomers of α-HCH and o,p′-DDT were more prevalent than the (−)-enantiomers in most samples, whereas both racemic and nonracemic residues existed for o,p′-DDD. These results implied that the SQG of chiral OCPs should be reassessed using concentrations of their individual enantiomers.