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Soil water deficit impacts cold acclimation and freezing tolerance in creeping bentgrass (Agrostis stolonifera L.), but the mechanisms underlying have not been well understood. The objectives of this study were to investigate the effects of deficit irrigation before and during cold acclimation on osmoprotectants, antioxidant metabolism, and freezing tolerance in creeping bentgrass. The grass was subjected to three-soil moisture levels: well-watered [100% container capacity (CC)], deficit irrigation induced-mild drought stress (60% CC), and severe drought stress (30% CC) for 35 days including 14 days at 24/20 °C (day/night) and then 21 days under cold acclimation treatment (2 °C) in growth chambers. Leaf proline and total soluble sugar (TSS) levels were higher in the grass under mild drought stress relative to that under severe drought stress. Superoxide (O2 −·), hydrogen peroxide (H2O2), and malondialdehyde (MDA) content were higher in the grass under severe drought relative to that under well-watered and mild drought stress at day 35. Mild drought stress increased catalase (CAT) and guaiacol peroxidase (POD) activity, induced new isoforms and increased band intensities of superoxide dismutase (SOD), CAT, and POD during cold acclimation (days 14 to 35). No differences in osmoprotectants, antioxidant metabolism, and freezing tolerance were found between mild drought and well-watered treatments. The results of this study suggest deficit irrigation-induced mild drought stress in late fall and winter could induce accumulation of osmoprotectants and improve antioxidant metabolism, and freezing tolerance, but severe drought stress could reduce freezing tolerance of creeping bentgrass in the region with limited precipitation.