Time Matters vs LawToolBox

Time Matters7.6Visit LawToolBox4.0Visit

Higher score Time Matters #4 in Legal Calendar Software 7.6/10 From $950/user ✓ 1 of 1 features Visit Time Matters

vs

LawToolBox #5 in Legal Calendar Software 4.0/10 7-day trial ✓ 0 of 1 features Visit LawToolBox

• Time Matters fits best

  Firms needing established docketing and calendars

• LawToolBox fits best

  Microsoft 365 firms needing automated rule deadlines

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Side by side

Feature	Time Matters 7.6/10 Visit ↗	LawToolBox 4.0/10 Visit ↗
At a glance
Editor score	7.6	4.0
Ranking	#4 in Legal Calendar Software	#5 in Legal Calendar Software
Best for	Firms needing established docketing and calendars	Microsoft 365 firms needing automated rule deadlines
Pricing model	Paid	Paid
Starting price	Not published	Not published
Free plan	—	—
Free trial	—	—
Support	Phone, Docs	Email, Phone, Tickets, Docs
Integrations	8 integrations	20 integrations
Built for	Solo, Small business, Mid-market, Enterprise	Small business, Mid-market, Enterprise
Features Time Matters 1/1 · LawToolBox 0/1
Matter linking	✓ (best)	Not published
Specs
Deadline calculation	Not published	Automated
Court-rule coverage	Not published	Not published
Calendar sync	Not published	Not published
Reminder channels	Not published	Email
Mobile access	Not published	Not published
Our review
Pros	Links contacts, notes, events and calls to matters Combines docketing, scheduling, alerts and real-time firm calendars Integrates with Outlook and legal billing products	Calculates trigger-based deadlines across thousands of jurisdictions Connects matters, documents, and calendars within Microsoft 365 AI extracts deadlines from legal documents and supports legal-platform integrations
Cons	The first concurrent-user license starts at $950 one time Annual maintenance renewal starts at $350 for the first user Calendar features do not document legal rule-based deadline calculation	Calendar synchronization is one-way Cloud deployment only Trial is limited to 5 calculations or 7 days
Our verdict	Time Matters brings case and practice management together for law firms, legal departments and other organizations. Its calendar capabilities include docketing, scheduling, real-time firm calendars, alerts and reminders, with events tied… Read the review →	LawToolBox is cloud software for law firms, legal departments, courts, and agencies managing litigation deadlines and related matters. Its rules-based engine calculates dates from trigger events using court-specific rulesets across… Read the review →

Strengths and trade-offs

• Time Matters — where it wins

  • Links contacts, notes, events and calls to matters
  • Combines docketing, scheduling, alerts and real-time firm calendars
  • Integrates with Outlook and legal billing products

  Where it doesn't

  • The first concurrent-user license starts at $950 one time
  • Annual maintenance renewal starts at $350 for the first user
  • Calendar features do not document legal rule-based deadline calculation

• LawToolBox — where it wins

  • Calculates trigger-based deadlines across thousands of jurisdictions
  • Connects matters, documents, and calendars within Microsoft 365
  • AI extracts deadlines from legal documents and supports legal-platform integrations

  Where it doesn't

  • Calendar synchronization is one-way
  • Cloud deployment only
  • Trial is limited to 5 calculations or 7 days

• Time Matters7.6/10 · From $950/user

  Matter-linked calendars and docketing for firms accepting a one-time license cost.

  Visit Time MattersFull verdict →
• LawToolBox4.0/10 · 7-day trial

  Automates jurisdiction-specific deadlines and matter workflows inside Microsoft 365.

  Visit LawToolBoxFull verdict →