Recently, research is emerging highlighting the potential of cannabinoids' beneficial effects related to anxiety, mood, and sleep disorders as well as pointing to an increased use of cannabinoid-based medicines since COVID-19 was declared a pandemic. The objective of this research is 3 fold: i) to evaluate the relationship of the clinical delivery of cannabinoid-based medicine for anxiety, depression and sleep scores by utilizing machine learning specifically rough set methods; ii) to discover patterns based on patient features such as specific cannabinoid recommendations, diagnosis information, decreasing/increasing levels of clinical assessment tools (CAT) scores over a period of time; and iii) to predict whether new patients could potentially experience either an increase or decrease in CAT scores. The dataset for this study was derived from patient visits to Ekosi Health Centres, Canada over a 2 year period including the COVID timeline. Extensive pre-processing and feature engineering was performed. A class feature indicative of their progress or lack thereof due to the treatment received was introduced. Six Rough/Fuzzy-Rough classifiers as well as Random Forest and RIPPER classifiers were trained on the patient dataset using a 10-fold stratified CV method. The highest overall accuracy, sensitivity and specificity measures of over 99% was obtained using the rule-based rough-set learning model. In this study, we have identified rough-set based machine learning model with high accuracy that could be utilized for future studies regarding cannabinoids and precision medicine.