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- Radio Shack
- Radio Society of Ontario
- Randall Farr Company
- Randall Farr & Company
- Ranger Brewing Company Limited
- Raphael Tuck & Sons Art Publishers
- Rapid Grip and Batten Limited
- Rathskellar Restaurant and Tavern
- Ratz Family
- Raymond Sewing Machine Company
- Raymond's Nut Shop
- Raymond's Nut Shops Limited
- RCA Records
- R.C. Company
- R.D. Lang and Company
- R.D. Lang & Company
- Reader's Digest
- Recreation Association Committee
- Red Cap Ale
- Red Cross
- Red Front Department Stores
- Reed Engraving Company Limited
- Rega Industries Limited
- Regina Hotel
- Regina Watch Company
- Regional Municipality of Waterloo
- Region of Waterloo
- Region of Waterloo Bylaw Enforcement
- Reid Brothers
- Reid Flying Service
- Reid Press Limited
- Reinharts Beverages
- Reinthal & Newman
- Reitzels Limited
- Reliable Toy Company
- Remembrance Day
- R.E. Sauder Limited
- Research in Motion
- Retail Shoe Association
- Rettinger Building Supplies Limited
- R. Forbes Company Ltd.
- Rickert Dairy
- Rickert's Dairy
- Rieck's Garage
- Risdon Manufacturing Company
- Ritepoint
- Riverside Park
- R-K Enterprises
- R. McDougall & Company
- R. McDougall Company Limited
- Robe and Clothing Company
- Robert Bell Engine & Thresher Company
- Robert Stewart Limited
- Robinson and Roe
- Robots Baseball Team
- Rochester Optical Company
- Rock Brewery
- Rock Island Lumber Company
- Rockway Gardens
- Rockway Municipal Golf and Bowling Club
- Rolph and Clark
- R & O Navigation Company
- Roschman Button Company
- Rosedale Creamery
- Rosedale Creamery Company
- Rosemount Dairy
- Rosemount Farm Dairy
- Rosemount Farms Dairy
- Roseville General Store
- Roseville School
- R.O. Smith Company
- Rotary Photo
- Rotary Photographic Series
- Rotograph Company
- Royal Bank
- Royal Canadian Airforce
- Royal Canadian Air Force
- Royal Canadian Army Service Corps
- Royal Canadian Electrical and Mechanical Engineers
- Royal Canadian Engineers
- Royal City Bottling Works
- Royal Hotel
- Royal Metal Company
- Royal Navy
- Royal Regiment of Canadian Artillery
- Royal Studio
- Royal Templars of Temperance
- Royal Tour
- Royalty Designs Inc.
- Royal Typewriter Company Inc.
- Royal Victoria Hospital
- Royal Visit
- Royal Visit 1939
- Royal Winter Fair
- Roy Studio
- Ruben Publishing Company
- Rumsey & Company
- Rumshi and Company