Dry forests in Sub-Saharan Africa are of critical importance for the livelihood of the local population given their strong dependence on forest products. Yet these forests are threatened due to rapid population growth and predicted changes in rainfall patterns. As such, large-scale woody cover monitoring of tropical dry forests is urgently required. Although promising, remote sensing-based estimation of woody cover in tropical dry forest ecosystems is challenging due to the heterogeneous woody and herbaceous vegetation structure and the large intra-annual variability in the vegetation due to the seasonal rainfall. To test the capability of Sentinel-2 satellite imagery for producing accurate woody cover estimations, two contrasting study sites in Ethiopia and Tanzania were used. The estimation accuracy of a linear regression model using the Normalised Difference Vegetation Index (NDVI), a Partial Least Squares Regression (PLSR), and a Random Forest regression model using both single-date and multi-temporal Sentinel-2 images were compared. Additionally, the robustness and site transferability of these methods were tested. Overall, the multi-temporal PLSR model achieved the most accurate and transferable estimations (R2 = 0.70, RMSE = 4.12%). This model was then used to monitor the potential increase in woody coverage within several reforestation projects in the Degua Tembien district. In six of these projects, a significant increase in woody cover could be measured since the start of the project, which could be linked to their initial vegetation, location and shape. It can be concluded that a PLSR model combined with Sentinel-2 satellite imagery is capable of monitoring woody cover in these tropical dry forest regions, which can be used in support of reforestation efforts.