| WINTERCROFT 1771930 · TMA1018451 | Wintercroft Design Ltd | 9 Electronics11 Lighting14 Jewellery+5 | Registered | 2019 |
| WINTERPROOF 1159710 · TMA653101 | RANKA ENTERPRISES INC. | 24 Textiles25 Clothing | Registered | 2005 |
| WINTERCAST 2035804 · TMA1268110 | AccuWeather, Inc. | 42 Science | Registered | 2024 |
| WINTERPRO 1815993 · TMA993533 · design | Shandong Jinyu Tire Co. Ltd. | 12 Vehicles | Registered | 2018 |
| WINTERFLO 1730712 · TMA978528 | MILLER MANUFACTURING COMPANY | 11 Lighting | Registered | 2017 |
| WINTERPILL 1327088 · TMA700158 | NC Brands L.P. a Delaware limited partnership | 1 Chemicals | Registered | 2007 |
| WINTERBALL 1071596 · TMA612417 | Ontario Baseball Association, Inc. | 9 Electronics16 Paper41 Education | Registered | 2004 |
| WINTERBALL 0738768 · TMA434149 | an individual | 18 Leather24 Textiles25 Clothing | Registered | 1994 |
| WINTERCARE 0628258 · TMA367402 | OMS Investments, Inc. (a Delaware corporation) | 1 Chemicals | Registered | 1990 |
| WinterCity 0917817 | CITY OF TORONTO | 1 Chemicals2 Paints3 Cosmetics+42 | Pending | 2006 |
| WINTERFROST 1980031 · TMA1267748 | The Procter & Gamble Company | 5 Pharmaceuticals | Registered | 2024 |
| WINTERARMOR 1808518 · TMA1053225 | PPG Architectural Finishes, Inc. | 2 Paints | Registered | 2019 |
| WINTERCRAFT 1580261 · TMA856989 | Minnehaha Group, LLC | 4 Oils11 Lighting16 Paper+2 | Registered | 2013 |
| WINTERCRAFT 1576928 · TMA898345 | Kumho Tire Co., Inc. | 12 Vehicles | Registered | 2015 |
| WINTERSTONE 1295545 · TMA706413 · design | an individual | 7 Machines | Registered | 2008 |
| WINTERSTONE 0846640 · TMA505212 | an individual | 19 Building | Registered | 1998 |
| WINTERFROST 2356264 | Sugar Mountain Livestock, LLC | 29 Meat31 Fresh | Pending | 2024 |
| WINTERWORKS 2355264 | Owner not listed | 36 Finance | Pending | 2024 |
| WINTERCOMMAND 1897008 · TMA1075858 | The Goodyear Tire & Rubber Company | 12 Vehicles | Registered | 2020 |
| WinterContact 1149257 · TMA628170 | CONTINENTAL REIFEN DEUTSCHLAND GMBH | 12 Vehicles | Registered | 2004 |
| WINTERLICIOUS 0916133 | CITY OF TORONTO | 1 Chemicals2 Paints3 Cosmetics+42 | Pending | 2004 |
| WINTERTIME 2305170 · TMA1263387 | Owner not listed | 31 Fresh | Registered | 2024 |
| WINTERTIME 2129928 · TMA1222130 | PetSmart Home Office LLC | 28 Toys | Registered | 2024 |
| WINTERPLEX 2119385 · TMA1203978 | TIB MOLBIOL Syntheselabor GmbH | 1 Chemicals5 Pharmaceuticals | Registered | 2023 |
| Wondercomm 2114931 · TMA1182907 | Animis Global Inc. | 9 Electronics38 Telecommunications | Registered | 2023 |