| R H Farming Limited | Agriculture & fishing | 2014 |
| R J Pinkney Ltd | Professional & scientific | 2024 |
| R.F. Martin (Haulage) Limited | Transport & logistics | 1976 |
| R.J. Baker & Co. Limited | Agriculture & fishing | 1994 |
| Radonov Foods Ltd | Hospitality | 2024 |
| Rafters Electrical Ltd | Construction | 2015 |
| Rafters Wholesale Limited | Real estate | 2000 |
| Railton & Gale Limited | Professional & scientific | 2023 |
| Railton Services Limited | Administrative & support | 2002 |
| Rakhi Ltd | Transport & logistics | 2026 |
| Rankin Joinery Services (Yorkshire) Ltd | Construction | 2025 |
| Ravelle Scientific Limited | Information & communication | 2000 |
| Raysul Holdings Limited | Professional & scientific | 1986 |
| Rayviation Limited | Transport & logistics | 1998 |
| RB2000 Limited | Wholesale & retail | 2000 |
| Rclc Holdings Ltd | Financial services | 2025 |
| Rcsj Construction Ltd | Real estate | 2025 |
| Rcsj Investments Ltd | Real estate | 2024 |
| Rcsj Management Ltd | Financial services | 2026 |
| Red ASB Limited | Manufacturing | 1992 |
| Red Hot Catering Equipment Limited | Administrative & support | 1990 |
| Red Retail Products Ltd | Other services | 2002 |
| Red Rhino Plant Hire Limited | Administrative & support | 2015 |
| Redcarr Ltd | Construction | 2017 |
| Redman Butler | Professional & scientific | 2015 |
| Redman Nichols Butler | Professional & scientific | 2015 |
| Redsoft Technology Limited | Information & communication | 2014 |
| Refrigeration on the Wolds Limited | Manufacturing | 2002 |
| Reinventer Limited | Manufacturing | 2012 |
| RENOV8 Group Inc Ltd | Construction | 2024 |
| Renwick & Renwick Limited | Professional & scientific | 2018 |
| Repeat CNC Ltd | Manufacturing | 2023 |
| Replacement Auto Supplies Ltd | Manufacturing | 2015 |
| Resort Leisure (Willow Lakes) Limited | Construction | 2026 |
| Retail Engineering Design Limited | Manufacturing | 2004 |
| Rfid Systems Limited | Wholesale & retail | 2012 |
| Rhodes Roots & Remedies Limited | Education | 2021 |
| Richard Nicholson Limited | Agriculture & fishing | 1998 |
| Richard W. Tennant Limited | Agriculture & fishing | 1987 |
| Richards Bespoke Ironmongery Limited | Construction | 2008 |
| Richmond House Social Care Residential Ltd | Health & social care | 2021 |
| Richmond House Social Care Services CIC | Education | 2018 |
| Richmond Motor Services Limited | Wholesale & retail | 2006 |
| Rivadell Limited | Other services | 1987 |
| Riverbank Farm Limited | Agriculture & fishing | 2025 |
| Riverbank Retreats & Property Ltd | Real estate | 2025 |
| Riverhead Residents Association Limited | Households | 1973 |
| Riverhead Ultrasonic Ltd | Professional & scientific | 2015 |
| Riverside Clinic Limited | Health & social care | 2004 |
| RJH Scarborough Limited | Construction | 2024 |
| RM Bannister Farming Limited | Agriculture & fishing | 2015 |
| ROB Hatfield & SON Limited | Extraterritorial | 1996 |
| Robert Croft Ltd. | Transport & logistics | 2003 |
| Robert Heaps 2010 Limited | Financial services | 2010 |
| Robert Lindley Limited | Agriculture & fishing | 1998 |
| Rocket Publishing Co. Limited | Information & communication | 1953 |
| Rodm Kebab Limited | Hospitality | 2025 |
| Rolydiam Consultancy Limited | Professional & scientific | 2025 |
| Roma Trading Limited | Wholesale & retail | 2005 |
| RON Stork Fertiliser Services Limited | Other services | 2002 |
| RON Whitfield Limited | Manufacturing | 2012 |
| Rookscroft Ltd | Arts & recreation | 2023 |
| Roscoe Software Ltd | Information & communication | 2026 |
| Rosconie Property Maintenance Ltd | Construction | 2025 |
| Rose Cottage Bakery Limited | Extraterritorial | 2019 |
| Rose Cottage Pantry Limited | Extraterritorial | 2019 |
| Ross' Bars Limited | Hospitality | 2025 |
| Rothes and Aikenway Fishings Limited | Agriculture & fishing | 1962 |
| Route YC C.I.C. | Other services | 2021 |
| Routhorpe Lodge Limited | Real estate | 2023 |
| Rowan Software Limited | Information & communication | 2024 |
| RS Engineering Services Limited | Manufacturing | 2015 |
| RUC Ltd | Professional & scientific | 2019 |
| Russell Studios Ltd | Professional & scientific | 2020 |
| Rustic Riddle Ltd | Wholesale & retail | 2016 |
| Ruston Eggs Limited | Agriculture & fishing | 1998 |
| Ryders Customs Ltd | Manufacturing | 2021 |
| Ryedale Property Services (Malton) Limited | Construction | 2025 |
| S & M Munro Limited | Wholesale & retail | 2003 |
| S & S Associates Limited | Energy | 2012 |
| S J Savile & Sons Ltd | Agriculture & fishing | 2021 |
| S R Kilby Contractors Ltd | Agriculture & fishing | 2019 |
| S R Levitt Limited | Information & communication | 2007 |
| S.H.A.W. Motor Vehicle Engineers Limited | Wholesale & retail | 2009 |
| S.R.L Electrical Services Ltd | Construction | 2025 |
| Saag Property Group Ltd | Real estate | 2022 |
| Safecare Group Ltd | Wholesale & retail | 2021 |
| Saltrasu Holdings Limited | Financial services | 2022 |
| SAM Browne Foods Limited | Manufacturing | 1998 |
| Sand & Co Ltd | Real estate | 2013 |
| Sandhill Holdings Ltd | Financial services | 2025 |
| Sandsfield Gravel Company Limited | Water & waste | 1966 |
| Sandsfield Leisure Limited | Hospitality | 2017 |
| Sandsfield Limited | Financial services | 2017 |
| Santechnic Ltd | Construction | 2024 |
| Sarah J. Properties Ltd | Real estate | 2021 |
| Sausage Meat Supplies Ltd | Wholesale & retail | 2020 |
| SC Safety Ltd | Professional & scientific | 2016 |
| SCJ Agricultural Limited | Administrative & support | 2009 |
| SCJ Training Ltd | Administrative & support | 2015 |