- In 1996 the Library, seeking new means to enhance access and preservation of its collections, began the process of examining its collections for the purposes of digitization.
- In 1997, work began on The York Minutes and York/Toronto City Directories Pilot Project, a project to digitize and provide fulltext searching of selected 19th century Toronto directories.
- In 1999, the TPL Digital Collections website was launched with the content resulting from the directories project.
- In 2000, The Picturing the Past: Views of 19th and Early 20th Century Ontario Project on Ontario images was undertaken. The content was mounted on the Digital collections website in 2001.
- In 2001, the Historicity: Toronto Then and Now website was launched with historical and current information about the new city of Toronto and its neighbourhoods. The website brings together a wide variety of resources including a digital library of primary and secondary source materials from the Library's collections.
- In 2001, TPL also became a founding partner in Images Canada, a collaborative website that provides central search access to over 160,000 pictorial images held on the websites of participating Canadian cultural institutions.
- Also in 2001, TPL initiated the creation of virtual exhibitions for the Library’s Virtual Exhibits
- In 2002, the Canadian Theatre Record website was launched. The website includes searchable digital collections related to contemporary professional theatre in Canada - photographs, designs, posters, and theatre programs.
- In 2004, the Ontario History Quest website, a student learning resource dedicated to discovering Ontario's history, was launched. The website has curriculum-based learning content and searchable databases of primary and secondary source materials.
- In 2005/6, the Digital Collections website and its associated websites (Historicity, Canadian Theatre Record, Ontario History Quest) were migrated to a new technical environment that provides sites that are easier to use with added functionality.
- Also in 2005/6, the Library developed Phase Two of the Ontario History Quest website, adding new content and interactive features, as well as a French language website, En quête de l'histoire ontarienne.
- In 2006 the Library became a partner and contributed 300 historical publications to the Internet Archive project.
- In 2007 the newly migrated Digital Collections, Historicity, Canadian Theatre Record and Ontario History Quest websites were launched.