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The prevalence and spread of online misinformation during the 2020 US presidential election served to perpetuate a false belief in widespread election fraud. Though much research has focused on how social media platforms connected people to election-related rumors and conspiracy theories, less is known about the search engine pathways that linked users to news content with the potential to undermine trust in elections. In this paper, we present novel data related to the content of political headlines during the 2020 US election period. We scraped over 800,000 headlines from Google's search engine results pages (SERP) in response to 20 election-related keywords—10 general (e.g., "Ballots") and 10 conspiratorial (e.g., "Voter fraud")—when searched from 20 cities across 16 states. We present results from qualitative coding of 5,600 headlines focused on the prevalence of delegitimizing information. Our results reveal that videos (as compared to stories, search results, and advertisements) are the most problematic in terms of exposing users to delegitimizing headlines. We also illustrate how headline content varies when searching from a swing state, adopting a conspiratorial search keyword, or reading from media domains with higher political bias. We conclude with policy recommendations on data transparency that allow researchers to continue to monitor search engines during elections.