Background: There is little and heterogeneous knowledge on the links between the temperamental predispositions of psychopathology and the contemporary dimensional models of psychopathology, such as the Hierarchical Taxonomy of Psychopathology (HiTOP) classification system, which can be aligned with the five-factor model (FFM) of personality. This meta-analysis seeks to expand the temperamental theoretical basis of the HiTOP model by incorporating associations of temperament traits of two temperamental theories measured, respectively, by the Temperament and Character Inventory (TCI) and the Temperament Evaluation of Memphis, Pisa, Paris, and San Diego Autoquestionnaire (TEMPS-A) with (a) the FFM’s personality domains and (b) HiTOP’s five psychopathological spectra. Methods: A systematic search was done on Web of Science, Scopus, PubMed, ProQuest, Cochrane Database, and Google Scholar for all articles published in English from January 1990 to August 2020. Because of heterogeneity in the results of almost 70% of studies, pooled estimates of correlation coefficients were calculated using the random-effects method. Risk of bias (low-quality studies) and publication bias are reported. Results: The pooled correlations obtained from the analysis of 35 studies showed that the temperamental profile associated with each FFM domain and HiTOP spectra is distinct. Specifically, TCI-harm avoidance (HA) and all TEMPS temperaments were more strongly related to neuroticism/internalizing, extraversion/low detachment, and conscientiousness/disinhibition. In contrast, TCI-novelty seeking was more strongly related to both disinhibited/antagonistic externalizing and thought disorder. Conclusions: A large body of research supports maladaptive variants of all FFM domains and some psychopathological spectra of HiTOP related to the abnormal-range temperaments.