| Richard Joosten Design | Ontario |
| Richmond Software | Ontario |
| Richmond Systems Ltd | British Columbia |
| Richsoft Technologies | |
| Rick's Fix Computer Repair | Saskatchewan |
| Rickyel | Quebec |
| Ricoh Canada, Inc. | |
| Ricon Consulting, Inc | Ontario |
| RICSAN Enterprises | Saskatchewan |
| RIDDL | New Brunswick |
| Ridegell Consulting, Inc. | |
| RideShark Corporation | |
| Ridgeway Computers | |
| Rigarus Construction, Inc. | Ontario |
| Rigel Kent Security and Advisory Services | Ontario |
| Rigelix | |
| Right Studio | Nova Scotia |
| Rigstar Industrial Telecom | |
| Riicon Technologies | |
| Riipen | |
| Rikibo, Inc. | |
| Riman Agency | |
| Rimmer Technology Partners | |
| Rimouski Informatique | Quebec |
| Rimrock Corporation | Ontario |
| Rinax Computer Systems | |
| Rinax Systems Ltd | Alberta |
| RingCentral, Inc. | Ontario |
| Rio Partners Management, Inc. | |
| Riopel Consultant, Inc. | Quebec |
| RIP Tutorial | |
| rippelapp Technologies, Inc. | |
| Ripple | |
| Ripple Therapeutics | |
| Ripple Ventures | Ontario |
| RISC Capital | |
| Rise Controls | Ontario |
| Rise Fintech, Inc. | |
| Rise Marketing SEO Agency | |
| Rise Vision, Inc. | Ontario |
| RISIMS | Ontario |
| Rising Telecom | Ontario |
| Riskfuel Analytics, Inc. | |
| Risolv IT Solutions | Ontario |
| Rithmik | |
| Ritual Technologies, Inc. | |
| Riva | Alberta |
| Rival Technologies | |
| Rivan Media | Ontario |
| Rivendell Software | Nova Scotia |