Purpose Lack of progress advancing labour provisions in multilateral trade instruments has led some countries to develop their own labour chapters in bilateral and plurilateral trade agreements. This study aims to track the evolution of 25 years of labour chapters in Canadian trade agreements. Design/methodology/approach Modelled on Hoekman (1995), the authors present a novel index using the International Labour Organization’s (ILO) core labour standards to compare and evaluate ambition and enforcement in Canada’s labour chapters. Findings The quality of Canada’s labour chapters has steadily improved from 1994 to 2020, with scores rising from 46 to 91 out of 100. In addition, Canada has used its negotiating leverage to encourage partners with weak labour regimes to make improvements. Yet, the highest quality chapters were achieved with trade partners similar to Canada, and those chapters have not pushed either party to improve their own domestic labour regimes. The authors discuss the limits of the ILO standards for addressing contemporary debates about labour and trade. Originality/value The authors’ assessment provides the first empirical evidence to demonstrate that Canada’s labour chapters have evolved over time, and that the origins of this evolution predate the Liberal government’s progressive trade agenda by several decades. The authors also suggest that Canada’s “middle road” compromise on ambition versus enforceability may increase the relevance of the index for research on other middle powers and potentially countries in the global south.