Yes / Event monitoring is an essential application of Smart City platforms. Real-time monitoring of gully and drainage blockage is an important part of flood monitoring applications. Building viable IoT sensors for detecting blockage is a complex task due to the limitations of deploying such sensors in situ. Image classification with deep learning is a potential alternative solution. However, there are no image datasets of gullies and drainages. We were faced with such challenges as part of developing a flood monitoring application in a European Union-funded project. To address these issues, we propose a novel image classification approach based on deep learning with an IoT-enabled camera to monitor gullies and drainages. This approach utilises deep learning to develop an effective image classification model to classify blockage images into different class labels based on the severity. In order to handle the complexity of video-based images, and subsequent poor classification accuracy of the model, we have carried out experiments with the removal of image edges by applying image cropping. The process of cropping in our proposed experimentation is aimed to concentrate only on the regions of interest within images, hence leaving out some proportion of image edges. An image dataset from crowd-sourced publicly accessible images has been curated to train and test the proposed model. For validation, model accuracies were compared considering model with and without image cropping. The cropping-based image classification showed improvement in the classification accuracy. This paper outlines the lessons from our experimentation that have a wider impact on many similar use cases involving IoT-based cameras as part of smart city event monitoring platforms. / European Regional Development Fund Interreg project Smart Cities and Open Data REuse (SCORE).