Cercospora leaf spot of olive (CLSO), caused by Pseudocercospora cladosporioides, is one of the most important foliar diseases of olives worldwide. This study aimed to evaluate the effect of a wide range of fungicides on mycelial growth and conidial germination of P. cladosporioides in vitro, and to evaluate the effect of several fungicides, application timings and management strategies (conservative and risky) to control CLSO under field conditions. Of the studied fungicides, strobilurin compounds and benomyl were the most effective active ingredients, followed by folpet, captan and maneb, in inhibiting mycelial growth and conidial germination. The pyraclostrobin + boscalid treatment was effective under field conditions, even without the application of supplementary copper. Treatments conducted in October or March were more effective than those conducted in May. Management strategies based on the author's experience reduced copper applications up to 32.0% and 50.0% (conservative and risky strategy, respectively) in comparison to the reduction with the traditional strategy, without increasing CLSO incidence. This work provides useful information about effective formulations against CLSO and a reduction in unnecessary fungicide applications in an effort to implement IPM in olive orchards under Mediterranean conditions.