Yield of sweet cherry (Prunus avium L.) is determined by fruit set, a developmental stage sensitive to variable spring environmental conditions. To sustain fruit production and enhance crop climate resilience, it is important to understand the impacts of abiotic stresses and the effectiveness of horticultural mitigations in the spring on the critical developmental processes during fruit set. In this study, flowering phenology, pistil browning and percent fruit set of ‘Lapins’ were monitored at five sites of different elevation and frost risk in the Okanagan Valley, British Columbia, Canada, in 2019 and 2022. At Site 1 in Summerland Research and Development Centre (“SuRDC1”), where a ‘Lapins’ on Krymsk 5 planting was located in a frost pocket where the crops were exposed to high risk of cold damage in the spring, a series of experiments were conducted to investigate the floral organ viability and percent fruit set under low temperatures, and under the effects of four spring horticultural mitigation measures. Installation of polyethylene sleeves and FAME spray (fatty acid methyl esters-based plant growth regulator, WAIKEN, SST Australia) were implemented in 2019; boric acid spray and postponed irrigation were tested in 2022. Low fruit set at SuRDC1 in both years was associated with severe pistil browning after night temperature dropped below −4 °C in late April. In 2019, the semi-enclosure of polyethylene sleeves led to an increase in the surface temperature (Tsurfae) of floral buds by 2–4 °C, which prolonged the stage of first bloom, delayed petal fall and prevented frost damage on pistils, but led to the decrease in percent fruit set by 77%, due to ovule abortion or cessation of fruitlet development. The early and late sprays of FAME had no significant influence on either abundance of germinated pollen tubes or percent fruit set; however, the potential of late spray in improving pollen abundance and reducing pistil browning requires further investigation. In 2022, the spray of 0.01% boric acid solution led to a decrease in fruit set by 6.95%. Six-week postponement of irrigation starting from full bloom decreased soil moisture, but increased soil temperature and improved fruit set by 7.61%. The results improved our understanding about the damages of adverse spring air temperatures on pistils and ovules, and suggested the potential of irrigation adjustment in regulating soil moisture and temperature and improving fruit set in the cool and moist spring.