Some six decades of socialisation by the ruling People's Action Party (PAP) has ingrained in a majority of Singaporeans the instinct that it is not unusual to give up certain personal liberties for the greater good as long as the PAP State ensures the material well-being of Singaporeans. The general election of 2020 (GE2020) during the COVID-19 pandemic, put this social compact between the people and the State to the test. Significant job losses, wage cuts, and an erosion of personal wealth - due to measures to counter the pandemic - cut substantially into the PAP popular vote nationally, and resulted in an unprecedented 10 candidates from the opposition Workers' Party (WP) being elected to Parliament. GE2020 confirmed the trend from GE2011, when the WP first made a breakthrough, that Singaporeans will only accept a party in moderate opposition to the PAP. This narrative differs markedly from conventional wisdom. Breakthrough 2.0 explores the aforementioned phenomena. The book analyses critically the issues surrounding parliamentary elections in Singapore. It also focuses on issues not explored by many other observers, namely voter psychology; election processes; and, party branding. A comparative analysis of election practices and processes in other jurisdictions is also employed to determine where parallels can or cannot be drawn with the situation in Singapore. The author has had direct access to personalities across the political parties. Consequently, he utilises primary sources, supported by evidence, in sketching out backstories to events which exposes certain myths that were prevailing in social media in the months running up to GE2020.