| Richard Lamming Ltd | Construction | 2014 |
| Richard Mace Associates Limited | Professional & scientific | 2020 |
| Richard Martin Renewables Limited | Agriculture & fishing | 2014 |
| Richard Percival Ltd | Transport & logistics | 2021 |
| Richard Steenberg Limited | Professional & scientific | 2004 |
| Richardson & Starling (Northern) Limited | Construction | 1968 |
| Richardsons Estates Ltd | Real estate | 2025 |
| Richmond (North Yorkshire) Physiotherapy Practice Limited | Health & social care | 2004 |
| Richmond Heights (Spring) Limited | Health & social care | 2019 |
| Richmond Heritage Limited | Hospitality | 2022 |
| Rickerby Estates Limited | Agriculture & fishing | 2003 |
| Rickerby Fuels Limited | Professional & scientific | 1961 |
| Rickerby Gardens Management Limited | Households | 2003 |
| Rickerby Retreat Limited | Other services | 2012 |
| Ridge Close Management Limited | Households | 2021 |
| Right Finance Limited | Financial services | 2020 |
| Right Your Own Story Ltd | Other services | 2017 |
| Riley Rentals Ltd | Real estate | 2024 |
| Ringwood DSP Limited | Other services | 2025 |
| Rippon Medical Services Limited | Health & social care | 2012 |
| Riqueza Multibusiness Group of Company Ltd | Wholesale & retail | 2025 |
| RIS Technical Solutions Ltd | Other services | 2021 |
| Riterent Limited | Real estate | 2025 |
| Ritson Wharf Limited | Households | 1990 |
| River Communications Limited | Extraterritorial | 2011 |
| Riverbrook Gardens (Alnwick) Management Company Limited | Real estate | 2022 |
| Riverside Caravan Park (Hawick) Limited | Hospitality | 2000 |
| Rizqmart Ltd | Wholesale & retail | 2025 |
| RJ & CA Associates Limited | Wholesale & retail | 2014 |
| RJ Hick Building Ltd | Construction | 2022 |
| RJ Plumbing & Heating (Cumbria) Limited | Construction | 2019 |
| Rj&Cs Ltd | Real estate | 2025 |
| RJB Carlisle Ltd | Other services | 2023 |
| RJB Tech Limited | Manufacturing | 2012 |
| RJD Masonry Ltd | Construction | 2020 |
| RJM Planning Consultant Ltd | Professional & scientific | 2024 |
| RJO Delivery Ltd | Transport & logistics | 2023 |
| Rkeytec Limited | Information & communication | 2009 |
| RLM Joinery & Building Ltd | Construction | 2012 |
| RM & N Wainwright & SON Limited | Agriculture & fishing | 2001 |
| RM Clayton Limited | Professional & scientific | 2026 |
| RM Property & Assets Limited | Real estate | 2023 |
| Rmaradu Ltd | Transport & logistics | 2021 |
| RMW Property Ltd | Real estate | 2019 |
| RO (Scotby) Limited | Hospitality | 2024 |
| Road Rail Rentals Limited | Transport & logistics | 2004 |
| Roadhead Auction Mart Management Ltd | Real estate | 2005 |
| Robert Little Garages Limited | Wholesale & retail | 2005 |
| Robert Todd & SON Limited | Wholesale & retail | 2000 |
| Robert Todd FAR East Limited | Wholesale & retail | 2023 |
| Robert Todd Holdings Limited | Real estate | 2019 |
| Robert Todd Yarn Limited | Wholesale & retail | 2023 |
| Robin Steel Land Agency Ltd | Professional & scientific | 2019 |
| Robinson Drafting and Design Limited | Professional & scientific | 2019 |
| Robinson Fields (Murton) Management Company Limited | Real estate | 2023 |
| Robson Medical and Mobility Limited | Health & social care | 2012 |
| Robsons Haulage Limited | Transport & logistics | 2000 |
| Robyn Gray Equestrian Limited | Agriculture & fishing | 2023 |
| Rocket Link Ltd | Professional & scientific | 2021 |
| Rocktree Consulting Ltd | Professional & scientific | 2017 |
| Roebuck Investment Limited | Wholesale & retail | 2019 |
| Roebuck Pastures Management Company Limited | Households | 2021 |
| Rokpa Trust | Health & social care | 1996 |
| Rolands Repairs Ltd | Other services | 2025 |
| Rolling PUB Company (Cumbria) Limited | Hospitality | 2021 |
| Romans Paving Ltd | Administrative & support | 2023 |
| Romans Way November | Financial services | 2022 |
| Romans Way Properties | Real estate | 2017 |
| Rome Street Gasworks Ltd | Real estate | 2019 |
| Rome Street Holdings Ltd | Real estate | 2017 |
| Rome Street Junction Ltd | Other services | 2017 |
| Romeo Soare 05 Ltd | Transport & logistics | 2025 |
| RON Forster & SON Limited | Construction | 2005 |
| Ronan Construction Civil Engineering Services Limited | Construction | 2011 |
| Roof Tiles Technology Limited | Professional & scientific | 2001 |
| Room 26 Limited | Wholesale & retail | 2014 |
| Room 33 Hair by Lauren Limited | Other services | 2025 |
| Roosevelt & Co. Ltd | Wholesale & retail | 2025 |
| Root Developments Limited | Real estate | 2013 |
| Root TEN Limited | Professional & scientific | 2014 |
| Rope Access (Cumbria) Limited | Administrative & support | 2019 |
| Ropheka Care Solution Ltd | Health & social care | 2025 |
| Rose and Thistle Carlisle Limited | Hospitality | 2019 |
| Rose Bank Sawmill Limited | Manufacturing | 2003 |
| Rose Beauty and Nail Studio Ltd | Other services | 2026 |
| Rose Castle Company Limited | Hospitality | 2016 |
| Rose Nails Carlisle Ltd | Other services | 2021 |
| Rosegold Home Care Services Limited | Health & social care | 2020 |
| Rosehill Day Nursery Limited | Health & social care | 2021 |
| Rosewood Consultants Limited | Professional & scientific | 2018 |
| Rosie Limited | Hospitality | 2023 |
| Ross Developments and Rentals Ltd | Real estate | 2021 |
| Ross Innovation Ltd | Professional & scientific | 2023 |
| Rostore Limited | Other services | 2017 |
| Rota Property Ltd | Real estate | 2025 |
| Rouge ET Blue Limited | Hospitality | 2024 |
| Routledge Construction Consultancy Ltd | Professional & scientific | 2019 |
| Routledge Conveying Services Limited | Manufacturing | 2011 |
| Rowland Engineering Services Limited | Professional & scientific | 2013 |
| Roxy Marine Ltd | Wholesale & retail | 2024 |