An attempt is made in this paper to report how a supervised methodology has been adopted for the task of Word Sense Disambiguation (WSD) in Bengali with necessary modifications. At the initial stage, four commonly used supervised methods, Decision Tree (DT), Support Vector Machine (SVM), Artificial NeuralNetwork (ANN) and Naı¨ve Bayes (NB), are developed at the baseline. These algorithms are applied individually on a data set of 13 most frequently used Bengali ambiguous words. On experimental basis, the baseline strategyis modified with two extensions: (a) inclusion of lemmatization process into the system and (b) bootstrapping of the operational process. As a result, the levels of accuracy of the baseline methods are slightly improved, which is a positive signal for the whole process of disambiguation as it opens scope for further modification of the existing method for better result. In this experiment, the data sets are prepared from the Bengali corpus, developed in the Technology Development for Indian Languages (TDIL) project of the Government of India andfrom the Bengali WordNet, which is developed at the Indian Statistical Institute, Kolkata. The paper reports the challenges and pitfalls of the work that have been closely observed during the experiment.