Anal squamous cell carcinoma (ASCC) is an uncommon yet rising cancer worldwide. Definitive chemo-radiation (CRT) remains the best curative treatment option for non-metastatic cases in terms of local control, recurrence-free and progression-free survival. Still, despite overall good results, with 80% five-year survival, a subgroup of ASCC patients displays a high level of locoregional and/or metastatic recurrence rates, up to 35%, and may benefit from a more aggressive strategy. Beyond initial staging, there is no reliable marker to predict recurrence following CRT. Imaging, mostly positron emission tomography-computed tomography (PET-CT) and magnetic resonance imaging (MRI), bears an important role in the diagnosis and follow-up of ASCC. The routine use of radiomics may enhance the quality of information derived from these modalities. It is thought that including data derived from radiomics into the input flow of machine learning algorithms may improve the prediction of recurrence. Although some studies have shown glimmers of hope, more data is needed before offering practitioners tools to identify high-risk patients and enable extensive clinical application, especially regarding the matters of imaging normalization, radiomics process standardization and access to larger patient databases with external validation in order to allow results extrapolation. The aim of this review is to present a critical overview from this data.