This article examines how electoral outcomes nurture democratic sentiment. Elections generate winners and losers, and voters alter their beliefs in ways that are congruent with electoral choices. Yet, while winning and losing shape democratic sentiment, comparatively less is known about the intermediary influences through which this relationship flows. Analysing data from the Federal Republic of Germany, this article probes for contextually driven effects using cross-level modelling of German General Social Surveys (Allgemeine Bevölkerungs Umfrage der Sozialwissenschaften). Four hypotheses are tested at the individual level, with the results confirming the following. First, winners’ democratic sentiments remain firm in the context of electoral stalemate, but are mediated through their ideological proximity to the party for which they voted. Second, time conditions winners’ democratic sentiments, but in discrepant ways in the east and west of the country. There is no evidence that the western relationship has systematically weakened over a 20-year period. The eastern relationship, meanwhile, was especially strong following unification, but stabilised thereafter. In demonstrating that winners’ attitudes are influenced by political context and time, the article presents a more refined analysis and a more comprehensive account, and develops fresh lines of inquiry into the structure of mass democratic sentiment.