Civil society is currently marked by two major trends—one is the shrinking civic space, as civil society actors are increasingly met with ideological resistance, and the other is marketisation as New Public Management principles are introduced in civil society governance. This chapter explores how civil society leaders experience these macro-level trends through forms of contestation, which is a perspective that has so far been overlooked in research. The theoretical framework distinguishes between the target, the source, and the depth of the contestation. The empirical investigation is based on a new survey of civil society elites and compares leaders in Italy, Poland, Sweden, and the UK. Overall, the investigation finds less contestation than expected. Contestation of the leaders as individuals comes mostly from within their organisations and is more professional than ideological. More and deeper contestation is instead directed at the organisations, and its precise forms reflect the different civil society regimes that our four countries represent.