Plant breeders have long acknowledged parent-of-origin effects and their importance for parent selection, yet most of these effects remain uncharacterized and their basis remains unknown. In cucumber, the nuclear, mitochondrial, and chloroplast genomes are inherited biparentally, paternally, and maternally, respectively. Evaluation of reciprocal hybrids of double haploid (DH) cucumber lines offers a unique system for studying parent-of-origin effects associated with the organelles across identical nuclear backgrounds. Cucumber is a warm-season crop that is severely damaged by short periods of cold temperatures, and a maternally-inherited cold tolerance has been identified in the heirloom variety 'Chipper.' The first goal of this work was to characterize the phenotypic and genetic basis of cold tolerance conferred by 'Chipper' through evaluation of cold tolerant and susceptible reciprocal hybrids from crosses among DH lines. This work included cold recovery phenotyping in four different nuclear backgrounds, sequencing of the chloroplast genome and transcriptome to identify variants, as well as nuclear gene expression analysis and physiological assays to evaluate cold tolerance across two different nuclear backgrounds. The cold tolerance of 'Chipper' was associated with recovery from the cold treatments. A polymorphism in the chloroplast atpB gene conditioned an amino acid change that may be the genetic basis of the cold tolerance. Nuclear transcriptome analyses revealed no clearly shared differential gene expression between cold tolerant hybrids prior to cold treatment, consistent with the cold recovery phenotype and revealing the effect of nuclear background on expression of cold tolerance. The second goal of this work was to evaluate parent-of-origin effects on seed, cotyledon, and early growth in cucumber using a full diallel mating scheme using two DHs extracted from each of four populations. This work evaluated general combining abilities, specific combining abilities, and reciprocal effects across populations, DHs, and hybrid combinations. Transcriptome analyses of hybrids with significant reciprocal effects were performed and few common genes and processes were identified in mediating reciprocal effects on early growth phenotypes, consistent with significant specific combining abilities for these traits. These findings provide insights into specific parent-of-origin differences in cucumber and information useful for hybrid development. This work lays a foundation to warrant further investigation into the causative nature of the 'Chipper' chloroplast variant and beneficial reciprocal effects in cucumber.