Introduction: Following the rapid advances in minimally invasive surgery, there are a multitude of surgical modalities available for resecting rectal cancers. Robotic resections represent the current pinnacle of surgical approaches. Currently, decisions on the surgical modality depend on local resources and the expertise of the surgical team. Given limited access to robotic surgery, developing tools based on pre-operative data that can predict the difficulty of surgery would streamline the efficient utilisation of resources. This systematic review aims to appraise the existing literature on artificial intelligence (AI)-driven preoperative MRI analysis for surgical difficulty prediction to identify knowledge gaps and promising models warranting further clinical evaluation. Methods: A systematic review and narrative synthesis were undertaken in accordance with PRISMA and SWiM guidelines. Systematic searches were performed on Medline, Embase, and the CENTRAL Trials register. Studies published between 2012 and 2024 were included where AI was applied to preoperative MRI imaging of adult rectal cancer patients undergoing surgeries, of any approach, for the purpose of stratifying surgical difficulty. Data were extracted according to a pre-specified protocol to capture study characteristics and AI design; the objectives and performance outcome metrics were summarised. Results: Systematic database searches returned 568 articles, 40 ultimately included in this review. AI to support preoperative difficulty assessments were identified across eight domains (direct surgical difficulty grading, extramural vascular invasion (EMVI), lymph node metastasis (LNM), lymphovascular invasion (LVI), perineural invasion (PNI), T staging, and the requirement for multiple linear stapler firings. For each, at least one model was identified with very good performance (AUC scores of >0.80), with several showing excellent performance considerably above this threshold. Conclusions: AI tools applied to preoperative rectal MRI to support preoperative difficulty assessment for rectal cancer surgeries are emerging, with the progressing development and strong performance of many promising models. These warrant further clinical evaluation, which can aid personalised surgical approaches and ensure the adequate utilisation of limited resources.