Square Invoices vs FreshBooks
Side-by-side from the Top 11 ranking of The 11 Best Invoicing & Billing Software for Small Business (2026). 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
| Square Invoices | FreshBooks | |
|---|---|---|
| Top 11 rank | #6 / The 11 Best Invoicing & Billing Software for Small Business (2026) | #1 / The 11 Best Invoicing & Billing Software for Small Business (2026) |
| Score (out of 9.4) | 8.2 | 9.3 |
| Best for | Integrated with Square payments | Service businesses and freelancers |
| Pricing | $ ($0 with processing fees) | $$ ($19 to $60/mo) |
| HQ | San Francisco, USA | Toronto, Canada |
| Founded | 2009 | 2003 |
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 (2026)
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 (2026)
Methodology and scoring weights live at /methodology. No vendor pays for placement — see about.