Transforming critical infrastructure systems, such as water and energy, is crucial to achieving global sustainability and climate change targets in many cities. Whilst experimentation has been studied extensively in urban sustainability scholarships, there have been no large-N cross-sector comparative studies. Existing research is potentially blind to different patterns of urban experiments across multiple sectors. This is particularly relevant to advancing deep transitions thinking, which has increasingly foregrounded the notion of multi-system alignment across socio-technical domains. Our research aims to fill this knowledge gap using a database to characterise urban experiments across water and energy domains while integrating sectoral and place-based perspectives. We analysed 40 experiments across Melbourne and Adelaide, Australia. Our results show that on a collective level, these experiments skew towards technological interventions, while their transfer and impact trajectories are underpinned by distinct territorial and sectoral logics. We show that cross-sectoral analysis can reveal plurality in urban experiments across multiple systems and places while offering a more refined understanding of multi-system alignment requirements for deep transitions.