The exploration of children’s drawings as mathematical representations is a current focus in early years mathematics education research. This paper presents a qualitative analysis of 72 kindergarten to Grade 3 (5 to 8 years old) children’s drawings produced during problem-solving tasks centred on multiplicative strategies. Existing frameworks for the developmental sequence of mathematical drawings and the progression of children’s strategies for multiplicative situations were an interpretive lens through which to analyse the drawings. Children used pictographic and iconic drawing types to represent the “story” in the problem and the multiplicative strategies employed to solve the tasks. Exploration of the children’s drawings suggested that as children’s drawings become more structural, schematic in nature, it may be easier for children to show their understanding of the structural elements of multiplicative relationships. Results revealed that structural elements of multiplicative relationships were more easily seen in iconic representations; however, both pictographic and iconic drawings were useful to observe counting, additive, and multiplicative strategies when mathematical elements of the problem were visible. Additional representations attached to the drawings (e.g. numerical) were needed to confirm children’s strategies when their drawings lacked structure. These findings have implications for how young children’s drawings are interpreted by classroom teachers. The interpretation of these drawings suggested that some children may not yet realise how their drawings in mathematics need to shift from illustrations of the problem’s story context to representing mathematical ideas and processes — which requires intentional teaching of the purpose of drawings for mathematical contexts.