PurposeDuring the evaluation of European Capital of Culture (ECoC) Aarhus 2017, the evaluation organisation rethinkIMPACTS 2017 formulated a set of “dilemmas” capturing the main challenges arising during the design of the ECoC evaluation. This functioned as a framework for the evaluation process. This paper aims to present and discuss the relevance of the “Evaluation Dilemmas Model” as subsequently applied to the Galway 2020 ECoC programme evaluation.Design/methodology/approachThe paper takes an empirical approach including auto-ethnography and interview data to document and map the dilemmas involved in undertaking an evaluation in two different European cities. Evolved via a process of practice-based research, the article addresses the development of and the arguments for the dilemmas model and considers its potential for wider applicability in the evaluation of large-scale cultural projects.FindingsThe authors conclude that the “Evaluation Dilemmas Model” is a valuable heuristic for considering the endogenous and exogenous issues in cultural evaluation.Practical implicationsThe model developed is useful for a wide range of cultural evaluation processes including – but not limited to – European Capitals of Culture.Originality/valueWhat has not been addressed in the academic literature is the process of evaluating ECoCs; especially how evaluators often take part in an overall process that is not just about the evaluation but also planning and delivering a project that includes stakeholder management and the development of evaluation criteria, design and methods.