Between 1979 and 2018 Oxford University was presented with numerous opportunities to develop Southeast Asian Studies, nearly all of which were not taken up. This autobiographical article describes how these opportunities arose and how the author tried to generate support for Southeast Asian Studies during the period when he was Laithwaite Fellow in Modern History at Trinity College, Oxford (1979-2008) and following his early retirement in October 2008. The article describes the challenges of developing interest and commitment to area studies in a firmly Eurocentric Oxford history faculty, and the lack of institutional support from the wider University. This culminated in the embarrassing event at the Hong Kong Jockey Club in June 1988, when a substantial endowment for a chair of Nanyang (overseas Chinese) Studies offered by the Macao gambling tycoon, Stanley Ho, was allowed to slip out of the University’s grasp as a result of the ineptitude of its then Pro-Vice Chancellor, Sir Patrick Neill QC. Following that debacle, the article describes the author’s involvement in a number of parallel non-academic activities relating to Southeast Asia. These include lobbying in the University on East Timor, support for Daw Aung San Suu Kyi’s campaign for democracy in Burma through her Oxford-based husband, Dr Michael Aris, in the 1990s, and the establishment of the UK disability charity, The Cambodia Trust (1989-2014), and its spreads to East Timor (2003-5) and Indonesia (2008-12). Reference is also made in passing to the author’s involvement in a Track-2 diplomacy initiative aimed at normalizing US-Vietnam relations in 1989-90, and Oxford Project Southeast Asia initiative (2009-2018), an organization set up by Oxford graduate students from Southeast Asia, which hosted seven high profile Southeast Asian Studies Symposia in Oxford and in Southeast Asia between 2012 and 2018.