The fight against deforestation and forest degradation is now a major challenge for the preservation of global forest ecosystems. The remote sensing forest monitoring methods that are currently deployed are not always adapted to the Ivorian context because of the high cloud cover, diversity of shaded crops, and land clearing techniques. This study proposes a drone-based approach to assess intra-annual tree losses in the Bossématié classified forest. The method used is based on a detection analysis of tree losses in forest areas from a time series of aerial images acquired by drones from November 2018 to April 2019 on five sites in the studied forest. Based on photogrammetric models and photointerpretation, tree heights and tree crown sizes were estimated. Then, tree losses were detected based on the variation of tree heights during the study period. An analysis of the distribution of tree heights in Bossématié classified forest reveals that the maximum tree height was 65.06 m in November 2018 and 64.07 m in April 2019 with an average tree height of 34.29–37.00 m in November 2018 and 34.63–36.88 m in April 2019. The average tree crown area, meanwhile, was estimated to be 152 m². With an estimation accuracy of about 97%, these tree structural data indicate a minimum loss of 107 trees corresponding to a clearing area of 2 ha across all the surveyed sites from November 2018 to April 2019. This forest monitoring approach shows a considerable local loss of biodiversity and should be involved in the implementation of preservation, rehabilitation, and deployment strategies in an operational deforestation monitoring system in Côte d’Ivoire.