I've compiled a list of Toronto-based legaltech startups & established players:

30 Toronto-based Legal Technology Startups

Blue J Legalhttp://www.bluejlegal.com/Tax law assistance using IBM Watson
Capture.IThttp://getcaptureit.com/Billable hours time-tracking app
Clausehoundhttp://clausehound.com/Contract drafting and clause libraryLIZ
ClosingFoldershttp://www.closingfolders.com/Organizing and executing corporate dealsLegalX (MaRS)
Codify Legal Publishinghttp://www.codifylegalpublishing.com/Legal automation and publishingLIZ
CourtSide EDXhttp://www.edxontario.com/Service of legal documents
Diligenhttp://www.diligensoftware.com/Contract clause extraction (automated)LegalX (MaRS) + LIZ
Firmexhttp://www.firmex.com/Virtual data room SaaS
GhostPracticehttp://www.ghostpractice.ca/Practice management software
Global-Regulation.com*http://www.global-regulation.comWorld legislation search engine with translationsLegalX (MaRS)
Infotemshttp://www.infotems.com/Software for immigration law practices
Kabuk Lawhttps://www.kabuklaw.comLawyer discovery and appointment schedulingLIZ
Kinsohttp://www.kinso.ca/Family law matter managementLIZ
Knomoshttp://www.knomos.ca/Visualization of lawsLegalX (MaRS)
Korbitechttp://www.korbitec.ca/Automating court forms for civil litigation
Law Scouthttps://www.lawscout.ca/Hiring fixed-fee lawyers who work onlineLegalX (MaRS)
LawyerLinxhttps://www.lawyerlinx.com/Sourcing and receiving quotes for lawyersLIZ
Legal Linehttp://www.legalline.ca/Legal information in Q&A format
LegalCafehttp://www.legalcafe.ca/Online community for new lawyersLIZ
Legalswipehttp://www.legalswipe.com/Legal education app for criminal lawLIZ
Loom Analyticshttp://www.loomanalytics.com/Statistics for Ontario court decisions
MapYourPropertyhttp://www.mapyourproperty.com/Mapping land use/zoning information in the GTALIZ
MyLawBidhttp://www.mylawbid.com/Discover lawyers to hire
Nymityhttps://www.nymity.com/Privacy law compliance and legal information
Ontario Small Claims Wizardhttp://smallclaimswizard.com/Assists with filing Ontario Small Claims Court actionsLegalX (MaRS) + LIZ
rangefindrhttps://www.rangefindr.caResearching criminal sentencing ranges
StandInhttp://www.standin.is/Find a legal professional on short notice for court appearances
Syngrafiihttp://www.syngrafii.com/Signing and contract execution (e-signatures) LegalX (MaRS)
Teen Legal Helplinehttps://www.teenlegalhelpline.org/Legal help for teenagers (charity)
WorthIT Legalhttp://www.worthitsolutions.com/Sharepoint wiki software for lawyers

* = I am a co-founder

11 Established Toronto Legal Technology Businesses

Carswellhttp://www.carswell.com/corporate/about-us/The other legal publishing and information giant, known for Westlaw
Commonwealth Legalhttp://www.commonwealthlegal.com/Document management, primarily e-discovery
DivorceMate Softwarehttps://www.divorcemate.com/Family law software
Do Process Softwarehttp://www.doprocess.com/Primarily real estate conveyancing software (other areas too)
Emergenthttp://www.emergent.ca/Corporate minute book management and related services
Gavel & Gown Software Inc. (Amicus Attorney)https://amicusattorney.com/Lawyer practice management software
Infowarehttp://www.infoware.ca/Document automation and contract management software
Kirahttps://kirasystems.com/Contract analysis using machine learning
LexisNexis Canadahttp://www.lexisnexis.ca/en-ca/One of the two giants in legal publishing and information, known for QuickLaw
Teranethttp://www.teranet.ca/Property & real estate information, run Ontario land record system
Wolters Kluwerhttps://www.cch.ca/Tax law publishing & data products

The lists above are compiled from the portfolio companies of LIZ and LegalX, companies I know about, companies I've found through Google and listings on angel investment sites. It's far from a complete list so please send me your suggestions: addison@cameronhuff.com.

I've only listed startups that are active, have a software service or product, and appear to have their main office in Toronto (LIZ and LegalX both have non-Toronto startups). Note that some of the established players are Canadian subsidiaries of foreign companies that have a larger headquarters elsewhere.

Many consultancies provide custom software to lawyers but I haven't included them as they are more traditional IT/tech consulting businesses.

There's also my legal services marketplace: FlatLaw.ca. I don't charge for it yet but it's along the lines of some of the lawyer discovery services above. Undoubtedly there are many other similar projects that aren't full-time businesses but fall under the #legaltech banner. Please send me an email if you think your #legaltech service belongs on the list above.