Selective logging in tropical forests may lead to deforestation and forest degradation, so accurate mapping of it will assist in forest restoration, among other ecological applications. This study aimed to track canopy tree loss due to illegal logging of the important hardwood tree Ocotea usambarensis in a closed-canopy submontane tropical forest by evaluating the mapping potential of the very-high-resolution WorldView-3 multispectral dataset using random forest (RF) and support vector machine (SVM) with radial basis function kernel classifiers. The results show average overall accuracies of 92.3 ± 2.6% and 94.0 ± 2.1% for the RF and SVM models, respectively. Average kappa coefficients were 0.88 ± 0.03 for RF and 0.90 ± 0.02 for SVM. The user’s and producer’s accuracies for both classifiers were in the range of 84–100%. This study further indicates that vegetation indices derived from bands 5 and 6 helped detect canopy gaps in the study area. Both variable importance measurement in the RF algorithm and pairwise feature selection proved useful in identifying the most pertinent variables in the classification of canopy gaps. These findings could allow forest managers to improve methods of detecting canopy gaps at larger scales using remote sensing data and relatively little additional fieldwork.