This study explores the potential of olive leaves, long integral to Mediterranean traditional medicine, as a rich source of valuable compounds. The challenge lies in their considerable water content, hindering these compounds’ full valorization. Four drying methods (air-drying, oven-drying, freeze-drying and solar-drying) were investigated for their impact on nutrient and bioactive compound content in the leaves of four olive varieties (“Arbequina”, “Koroneiki”, “Menara” and “Picholine Marocaine”) cultivated in Morocco. In their fresh state, “Picholine Marocaine” exhibited the highest protein levels (6.11%), “Arbequina” had the highest phenolic content (20.18 mg gallic acid equivalents/g fresh weight (FW)), and “Koroneiki” and “Menara” were highest in flavonoids (3.28 mg quercetin equivalents/g FW). Specific drying methods proved optimal for different varieties. Oven-drying at 60 °C and 70 °C effectively preserved protein, while phenolic content varied with drying conditions. Air-drying and freeze-drying demonstrated effectiveness for flavonoids. In addition, an analytical approach using high-performance liquid chromatography and diode array detection (HPLC-DAD) was applied to investigate the effects of the different drying methods on the bioactive fraction of the analyzed samples. The results showed qualitative and quantitative differences depending on both the variety and the drying method used. A total of 11 phenolic compounds were tentatively identified, with oleuropein being the most abundant in all the samples analyzed. The freeze-dried samples showed the highest content of oleuropein in the varieties “Arbequina” and “Picholine Marocaine” compared to the other methods analyzed. In contrast, “Koroneiki” and “Menara” had higher oleuropein content when air dried. Overall, the obtained results highlight the importance of tailored drying techniques for the preservation of nutrients and bioactive compounds in olive leaves.