FreshBooks vs Square Invoices
Side-by-side from the Top 11 ranking of The 11 Best Invoicing & Billing Software for Small Business. Last verified June 20, 2026.
The short answer
FreshBooks ranks higher on Top 11 (#1 vs #6) for Small business owners and freelancers sending invoices and tracking payments. The most intuitive invoicing tool, perfect for service-based businesses and quick adoption.
At a glance
| FreshBooks | Square Invoices | |
|---|---|---|
| Top 11 rank | #1 / The 11 Best Invoicing & Billing Software for Small Business | #6 / The 11 Best Invoicing & Billing Software for Small Business |
| Score (out of 9.4) | 9.3 | 8.2 |
| Best for | Service businesses and freelancers | Integrated with Square payments |
| Pricing | $$ ($19 to $60/mo) | $ ($0 with processing fees) |
| HQ | Toronto, Canada | San Francisco, USA |
| Founded | 2003 | 2009 |
FreshBooks
The most intuitive invoicing tool, perfect for service-based businesses and quick adoption.
www.freshbooks.comSee full entry in The 11 Best Invoicing & Billing Software for Small Business
Square Invoices
The easiest invoicing choice for businesses already using Square for payments.
squareup.com/invoicesSee full entry in The 11 Best Invoicing & Billing Software for Small Business
Methodology and scoring weights live at /methodology. No vendor pays for placement — see about.