Deadline Assistant vs Time Matters

Deadline Assistant—Visit Time Matters7.6Visit

Deadline Assistant #1 in Legal Calendar Software —/10 Pricing on request ✓ 0 of 1 features Visit site

vs

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

• Deadline Assistant fits best

  Firms needing automated court-rule deadline control

• Time Matters fits best

  Firms needing established docketing and calendars

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Side by side

Feature	Deadline Assistant —/10 Visit ↗	Time Matters 7.6/10 Visit ↗
At a glance
Editor score	—	7.6
Ranking	#1 in Legal Calendar Software	#4 in Legal Calendar Software
Best for	Firms needing automated court-rule deadline control	Firms needing established docketing and calendars
Pricing model	Paid	Paid
Starting price	Not published	Not published
Free plan	Not published	—
Free trial	—	—
Support	Phone, Docs	Phone, Docs
Integrations	6 integrations	8 integrations
Built for	Small business, Mid-market, Enterprise	Solo, Small business, Mid-market, Enterprise
Features Deadline Assistant 0/1 · Time Matters 1/1
Matter linking	Not published	✓ (best)
Specs
Deadline calculation	Automated	Not published
Court-rule coverage	Not published	Not published
Calendar sync	Not published	Not published
Reminder channels	Email	Not published
Mobile access	Not published	Not published
Our review
Pros	Calculates deadlines from federal, state, and local court rules Creates custom templates, rule sets, and events for matter-specific workflows Tracks court-rule changes and supports role-based matter access	Links contacts, notes, events and calls to matters Combines docketing, scheduling, alerts and real-time firm calendars Integrates with Outlook and legal billing products
Cons	Calendar synchronization is one-way Available only through a web platform Pricing requires contacting sales	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
Our verdict	Deadline Assistant is legal calendaring software for law firms, legal departments, and matter teams that need deadlines tied to court rules. It calculates dates from applicable federal, state, and local rules, then centralizes deadline… Read the review →	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 →

Strengths and trade-offs

• Deadline Assistant — where it wins

  • Calculates deadlines from federal, state, and local court rules
  • Creates custom templates, rule sets, and events for matter-specific workflows
  • Tracks court-rule changes and supports role-based matter access

  Where it doesn't

  • Calendar synchronization is one-way
  • Available only through a web platform
  • Pricing requires contacting sales

• 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

• Deadline Assistant—/10 · Pricing on request

  Automates court-rule deadlines and organizes matter calendars for legal teams.

  Visit siteFull verdict →
• Time Matters7.6/10 · From $950/user

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

  Visit Time MattersFull verdict →