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Head-to-head · Legal Calendar Software

Deadline Assistant vs Time Matters

  • Updated Oct 2026
  • Both researched from official sources
  • 2 checks side by side
Higher score Deadline Assistant #1 in Legal Calendar Software 9.3/10 Pricing on request ✓ 0 of 1 features Visit site
Time Matters #4 in Legal Calendar Software 7.9/10 Paid ✓ 1 of 1 features Visit Time Matters

Deadline Assistant 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 scoreDeadline Assistant · 9.3/10
  • Most featuresTime Matters · 1 of 1

Deadline Assistant scores higher on our rubric for legal calendar software: 9.3 against 7.9 out of 10; our editors rank them #1 and #4.

Deadline Assistant is the better fit for firms needing automated court-rule deadline control. Time Matters is the better fit for firms needing established docketing and calendars.

  • Deadline Assistant fits best

    Firms needing automated court-rule deadline control

  • 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 Deadline Assistant 9.3/10 Visit ↗ Time Matters 7.9/10 Visit ↗
At a glance
Editor score 9.3 7.9
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 Pricing on request —
Free plan Not checked yet —
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 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 Email Not checked yet
Mobile access Not checked yet Not checked yet
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 →
  1. Deadline AssistantLegal Calendar Software 9.3Pricing on request
  2. Time MattersLegal Calendar Software 7.9Paid

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

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