Suggestions appear as you type. Use the up and down arrows to choose one and Enter to open it.

Head-to-head · Legal Calendar Software

CalendarRules vs Time Matters

  • Updated Sep 2026
  • Both researched from official sources
  • 2 checks side by side
CalendarRules #2 in Legal Calendar Software —/10 Pricing on request ✓ 0 of 1 features Visit CalendarRules
Higher score Time Matters #4 in Legal Calendar Software 7.6/10 From $950/user ✓ 1 of 1 features Visit Time Matters

CalendarRules leads on 0 checks, Time Matters on 1, and 1 is even. Who comes out ahead on the 2 yes/no, price and count checks where we have data for both products. The editor score weighs everything else too.

Our verdict

  • Highest scoreTime Matters · 7.6/10
  • Most featuresTime Matters · 1 of 1

Our editors rank CalendarRules at #2 and Time Matters at #4 for legal calendar software; CalendarRules has no rubric score yet (facts researched, not yet scored), so the checks below decide.

Time Matters offers matter linking; CalendarRules doesn't publish it.

CalendarRules is the better fit for firms needing broad, carefully maintained court rules. Time Matters is the better fit for firms needing established docketing and calendars.

  • CalendarRules fits best

    Firms needing broad, carefully maintained court rules

  • Time Matters fits best

    Firms needing established docketing and calendars

Advertiser disclosure: iTechGuides is reader-supported. We may earn a commission when you click some links. It never changes our verdict. How we rank.

Side by side

Feature CalendarRules —/10 Visit ↗ Time Matters 7.6/10 Visit ↗
At a glance
Editor score — 7.6
Ranking #2 in Legal Calendar Software #4 in Legal Calendar Software
Best for Firms needing broad, carefully maintained court rules Firms needing established docketing and calendars
Pricing model Paid Paid
Starting price Not published Not published
Free plan Not published —
Free trial — —
Support Email, Phone, Docs Phone, Docs
Integrations 8 integrations 8 integrations
Built for Solo, Small business, Mid-market, Enterprise Solo, Small business, Mid-market, Enterprise
Features CalendarRules 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 Not published Not published
Mobile access Not published Not published
Our review
Pros
  • Calculates deadlines from jurisdiction-specific rules, triggers, and service offsets
  • Covers federal, state, appellate, bankruptcy, local, judge, and specialty rules
  • Exports deadlines to Excel, iCal, Google Calendar, and Outlook
  • 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
  • Pricing is quote-based rather than publicly listed
  • Calendar sync is one-way, not two-way
  • Web-only access may not fit teams seeking other platforms
  • 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

CalendarRules is a cloud-based legal calendaring platform that calculates litigation deadlines from court rules. Its focus is firms that need jurisdiction-specific calculations across U.S. and Canadian courts, including rules tied to…

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 →
  1. CalendarRulesLegal Calendar Software —Pricing on request
  2. Time MattersLegal Calendar Software 7.6From $950/user

Strengths and trade-offs

  • CalendarRules — where it wins

    • Calculates deadlines from jurisdiction-specific rules, triggers, and service offsets
    • Covers federal, state, appellate, bankruptcy, local, judge, and specialty rules
    • Exports deadlines to Excel, iCal, Google Calendar, and Outlook

    Where it doesn't

    • Pricing is quote-based rather than publicly listed
    • Calendar sync is one-way, not two-way
    • Web-only access may not fit teams seeking other platforms
  • 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

More comparisons

Reviewed by iTechGuides Editors · Editorial team · Updated Sep 2026