Learning Design, as a field of research, provides practitioners with guidelines towards more effective teaching and learning. In parallel, observational methods (manual or automated) have been used in the classroom to reflect on and refine teaching and learning, often in combination with other data sources (such as surveys and interviews). Despite the fact that both Learning Design and classroom observation aim to support teaching and learning practices (respectively a priori or a posteriori), they are not often aligned. To better understand the potential synergies between these two strategies, this paper reports on a systematic literature review based on 24 works that connect learning design and classroom observations. The review analyses the purposes of the studies, the stakeholders involved, the methodological aspects of the studies, and how design and observations are connected. This review reveals the need for computer-interpretable documented designs; the lack of reported systematic approaches and technological support to connect the (multimodal) observations with the corresponding learning designs; and, the predominance of human-mediated observations of the physical space, whose applicability and scalability are limited by the human resources available. The adoption of ICT tools to support the design process would contribute to extracting the context of the observations and the pedagogical framework for the analysis. Moreover, extending the traditional manual observations with Multimodal Learning Analytic techniques, would not only reduce the observation burden but also support the systematic data collection, integration, and analysis, especially in semi-structured and structured studies.