Floods are the most recurrent, widespread and damaging natural disasters, and are ex-pected to become further devastating because of global warming. Blockage of cross-drainage hydraulic structures (e.g., culverts, bridges) by flood-borne debris is an influen-tial factor which usually results in reducing hydraulic capacity, diverting the flows, dam-aging structures and downstream scouring. Australia is among the countries adversely impacted by blockage issues (e.g., 1998 floods in Wollongong, 2007 floods in Newcas-tle). In this context, Wollongong City Council (WCC), under the Australian Rainfall and Runoff (ARR), investigated the impact of blockage on floods and proposed guidelines to consider blockage in the design process for the first time. However, existing WCC guide-lines are based on various assumptions (i.e., visual inspections as representative of hy-draulic behaviour, post-flood blockage as representative of peak floods, blockage remains constant during the whole flooding event), that are not supported by scientific research while also being criticised by hydraulic design engineers. This suggests the need to per-form detailed investigations of blockage from both visual and hydraulic perspectives, in order to develop quantifiable relationships and incorporate blockage into design guide-lines of hydraulic structures. However, because of the complex nature of blockage as a process and the lack of blockage-related data from actual floods, conventional numerical modelling-based approaches have not achieved much success. The research in this thesis applies artificial intelligence (AI) approaches to assess the blockage at cross-drainage hydraulic structures, motivated by recent success achieved by AI in addressing complex real-world problems (e.g., scour depth estimation and flood inundation monitoring). The research has been carried out in three phases: (a) litera-ture review, (b) hydraulic blockage assessment, and (c) visual blockage assessment. The first phase investigates the use of computer vision in the flood management domain and provides context for blockage. The second phase investigates hydraulic blockage using lab scale experiments and the implementation of multiple machine learning approaches on datasets collected from lab experiments (i.e., Hydraulics-Lab Dataset (HD), Visual Hydraulics-Lab Dataset (VHD)). The artificial neural network (ANN) and end-to-end deep learning approaches reported top performers among the implemented approaches and demonstrated the potential of learning-based approaches in addressing blockage is-sues. The third phase assesses visual blockage at culverts using deep learning classifi-cation, detection and segmentation approaches for two types of visual assessments (i.e., blockage status classification, percentage visual blockage estimation). Firstly, a range of existing convolutional neural network (CNN) image classification models are imple-mented and compared using visual datasets (i.e.,