Temporality is important for understanding Hong Kong's postcolonial status since its handover from Britain to China in 1997. This study examines the mediated regimes of postcolonial temporalities in coverage of five anniversaries of the Hong Kong handover (between 1998 and 2020) in Chinese and British newspapers. In 1998, the Chinese and British press shared a significant consensus regarding the “legitimate continuity” of Hong Kong's colonial legacies; however, this consensus was increasingly undermined by ideological contestations surrounding the city's postcolonial ruptures and differences. The multiple temporal claims that emerged in Chinese and British newspapers were systemized within a proposed framework that combined temporal modes (the “formal structures” of temporal relations) and ideological appraisals (the “general politics” where temporal modes are (il)legitimized and (ab)normalized). The temporal complexity concerning Hong Kong exemplifies the former colony's dilemmatic “in-betweenness” and temporal inconclusiveness, which create an open discursive space that invites ideological investments by powerful symbolic stakeholders.