This paper explores the problem of determining the time of an analogue wristwatch by developing two systems and conducting a comparative study. The first system uses OpenCV to find the watch hands and applies geometrical techniques to calculate the time. The second system uses Machine Learning by building a neural network to classify images in Tensorflow using a multi-labelling approach. The results show that in a set environment the geometric-based approach performs better than the Machine Learning model. The geometric system predicted time correctly with an accuracy of 80% whereas the best Machine Learning model only achieves 74%. Experiments show that the accuracy of the neural network model did increase when using data augmentation, however there was no significant improvement when adding synthetic data to our training set.