Chickpea is sensitive to cold stress, especially at reproductive stage, resulting in flower and pod abortion that significantly reduces seed yield. In the present study, we evaluated (a) whether cold acclimation imparts reproductive cold tolerance in chickpea; (b) how genotypes with contrasting sensitivity respond to cold acclimation; and (c) the involvement of cryoprotective solutes and antioxidants in anthers and ovules in cold acclimation. Four chickpea genotypes with contrasting cold sensitivity (cold-tolerant: ICC 17258, ICC 16349; cold-sensitive: ICC 15567, GPF 2) were grown in an outdoor environment for 40 days in November (average maximum/minimum temperature 24.9/15.9 °C) before being subjected to cold stress (13/7 °C), with or without cold acclimation in a controlled environment of walk-in-growth chambers. The 42-d cold acclimation involved 7 d exposure at each temperature beginning with 23/15 °C, 21/13 °C, 20/12 °C, 20/10 °C, 18/8 °C, 15/8 °C (12 h/12 h day/night), prior to exposing the plants to cold stress (13/7 °C, 12 h/12 h day/night; 700 μmol m−2 s−1 light intensity; 65–70% relative humidity). Cold acclimation remarkably reduced low temperature-induced leaf damage (as membrane integrity, leaf water status, stomatal conductance, photosynthetic pigments, and chlorophyll fluorescence) under cold stress in all four genotypes. It only reduced anther and ovule damage in cold-tolerant genotypes due to improved antioxidative ability, measured as enzymatic (superoxide dismutase, catalase, ascorbate peroxidase, and glutathione reductase) and non-enzymatic (ascorbate and reduced glutathione), solutes (particularly sucrose and γ-aminobutyric acid) leading to improving reproductive function and yield traits, whereas cold-sensitive genotypes were not responsive. The study concluded that cold tolerance in chickpea appears to be related to the better ability of anthers and ovules to acclimate, involving various antioxidants and cryoprotective solutes. This information will be useful in directing efforts toward increasing cold tolerance in chickpea.