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Head-to-head · Legal Calendar Software

CalendarRules vs Time Matters

  • Updated Oct 2026
  • Both researched from official sources
  • 2 checks side by side
Higher score CalendarRules #2 in Legal Calendar Software 8.8/10 Pricing on request ✓ 0 of 1 features Visit CalendarRules
Time Matters #4 in Legal Calendar Software 7.9/10 Paid ✓ 1 of 1 features Visit Time Matters

CalendarRules leads on 0 checks, Time Matters on 0, and 2 are 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 scoreCalendarRules · 8.8/10
  • Most featuresTime Matters · 1 of 1

CalendarRules scores higher on our rubric for legal calendar software: 8.8 against 7.9 out of 10; our editors rank them #2 and #4.

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. Vendors can pay for top positions in our rankings and for a place on other products' pages, and we may earn a commission when you click some links. Bought places stand at the number bought; this page and our disclosure say so. Paying vendors may get a fuller, more detailed review from our editors, and that review can change their score. How we rank.

Side by side

Feature CalendarRules 8.8/10 Visit ↗ Time Matters 7.9/10 Visit ↗
At a glance
Editor score 8.8 7.9
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 Pricing on request —
Free plan Not checked yet —
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 checked yet ✓ (best)
Specs
Deadline calculation Automated Not checked yet
Court-rule coverage Not checked yet Not checked yet
Calendar sync Not checked yet Not checked yet
Reminder channels Not checked yet Not checked yet
Mobile access Not checked yet Not checked yet
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 8.8Pricing on request
  2. Time MattersLegal Calendar Software 7.9Paid

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

All legal calendar software comparisons → · Full ranking →

Reviewed by iTechGuides Editors · Editorial team · Updated Oct 2026

Last updated · How we research and update