Meteorological parameters and occurrences of cracking (CR), russeting (RS), and sun scald (SS) symptoms were monitored in a pomegranate cv. “Wonderful” orchard planted in a W–E orientation, during a 3-year study. Moreover, the efficacy of preharvest foliar sprays with acetylsalicylic acid (ASA; 0.5 mM or 1.0 mM), applied biweekly four to six times, on yield and fruit quality attributes were evaluated in a 2-year study. Fruit from the N-side of the canopy had greater CR and RS, whereas SS symptoms were lower, compared with the S-exposed part of the canopy. The N-side of the canopy had also substantially lower fruit number and yield, suggesting for an important role of light on bisexual flower formation and/or fruit set. Following the occurrences in CR and RS during the fruit maturation period, it was found that temperature fluctuation was the main cause. The presence of RS damages may also be related with increased relative humidity and water movement as symptoms were higher in years with higher values, in the N-side of the canopy and often occurred in the exposed and stylar end of the fruit. The ASA treatment substantially reduced RS by up to 57%, improved the peel red coloration, while anthocyanin, antioxidant capacity, and soluble solid contents in juice were higher. Foliar sprays with ASA did not affect yield, but induced a trend of bigger-sized fruit. In conclusion, planting in a N–S row orientation and selecting an orchard plantation site with a minimum temperature fluctuation and low relative humidity during the fruit-ripening period are measures to control CR and RS in pomegranate. ASA foliar applications proved to have beneficial effects on juice antioxidant contents, but more importantly on fruit appearance.