The last two decades have experienced important and far-reaching changes to the retail landscape. In Australia, retail planning and management policies have sought to attract key players to particular sectors of the city thought to be most at risk of retail decline including CBD (central business district) locations. This study seeks to highlight the difficulty such strategies may face by quantifying the levels of retail investment into different locations. By mapping the direction retail investment has taken over time, the study explores the dichotomy which exists between the spatial dynamic of retail planning and retail investment in Australia. In conclusion, the analysis shows that, from an investment perspective, city centre locations are a much higher priced option and do not provide an excess return to justify the higher entry price. Should investment flows continue to be channelled away from these locations, the potential cycle of decline will be difficult to arrest and will pose major challenges for city planning authorities regarding the future vitality of city centres.