| 25 Nov 2018 - 10 Feb 2019 | Blithfield Barrel Winter Race Series at Blithfield (Monohulls above PY 845) | |
| 20 Jan 2019 | The Icicle Handicap Open Meeting at Bough Beech (Monohull dinghies) | |
| 20 Jan 2019 | Marlow Ropes Tipsy Icicle Series - Week 3 at Leigh & Lowton (Monohull dinghies) | |
| 26 Jan 2019 | Steve Nicholson Trophy at Northampton (Monohull dinghies) | |
| 26 Jan 2019 | Sutton Bingham Icicle at Sutton Bingham (Monohull dinghies) | |
| 27 Jan 2019 | The Icicle Handicap Open Meeting at Bough Beech (Monohull dinghies) | |
| 27 Jan 2019 | IRC GBR Inland Championship at Windermere Cruising Association (IRC yachts and IRC yachts) | |
| 27 Jan 2019 | Windermere Winter Series at Windermere Cruising Association (Sonata and SB20) | |
| 27 Jan 2019 | Marlow Ropes Tipsy Icicle Series - Week 4 at Leigh & Lowton (Monohull dinghies) | |
| 3 Feb 2019 | Marlow Ropes Tipsy Icicle Series - Week 5 at Leigh & Lowton (Monohull dinghies) | |
| 3 Feb 2019 | The Icicle Handicap Open Meeting at Bough Beech (Monohull dinghies) | |
| 9-10 Feb 2019 | Midwinter Regatta at Palm Beach, Florida (RS Aero) | |
| 10 Feb 2019 | The Icicle Handicap Open Meeting at Bough Beech (Monohull dinghies) | |
| 10 Feb 2019 | Exe Sails Roadford Rocket at Roadford Lake (Monohull dinghies) | |
| 10 Feb 2019 | Marlow Ropes Tipsy Icicle Series - Week 6 at Leigh & Lowton (Monohull dinghies) | |
| 10 Feb 2019 | Blithfield Barrel Winter Race Series - Day 4 at Blithfield (Monohull dinghies with PY greater than 845) | |
| 10 Feb 2019 | Windermere Winter Series at Windermere Cruising Association (Sonata and SB20) | |
| 10 Feb 2019 | IRC GBR Inland Championship at Windermere Cruising Association (IRC yachts and IRC yachts) | |
| 16 Feb 2019 | UK Winter Championships at The Oxford Blue at Oxford (RS Aero) | |
| 17 Feb 2019 | Marlow Ropes Tipsy Icicle Series - Week 7 at Leigh & Lowton (Monohull dinghies) | |
| 17 Feb 2019 | The Icicle Handicap Open Meeting at Bough Beech (Monohull dinghies) | |
| 18-22 Feb 2019 | RORC Caribbean 600 at Royal Ocean Racing Club (IRC and Class 40) | |
| 18 Feb 2019 | RORC Caribbean 600 at Antigua (IRC) | |
| 24 Feb 2019 | The Icicle Handicap Open Meeting at Bough Beech (Monohull dinghies) | |
| 24 Feb 2019 | IRC GBR Inland Championship at Windermere Cruising Association (IRC yachts and IRC yachts) | |
| 24 Feb 2019 | Windermere Winter Series at Windermere Cruising Association (Sonata and SB20) | |
| 24 Feb 2019 | Marlow Ropes Tipsy Icicle Series - Week 8 at Leigh & Lowton (Monohull dinghies) | |
| 2 Mar 2019 | Channel Chop at Portishead Cruising Club (Monohull dinghies) | |
| 3 Mar 2019 | Marlow Ropes Tipsy Icicle Series - Week 9 at Leigh & Lowton (Monohull dinghies) | |
| 10 Mar 2019 | Marlow Ropes Tipsy Icicle Series - Week 10 at Leigh & Lowton (Monohull dinghies) | |
| 10 Mar 2019 | Windermere Winter Series at Windermere Cruising Association (Sonata and SB20) | |
| 10 Mar 2019 | IRC GBR Inland Championship at Windermere Cruising Association (IRC yachts and IRC yachts) | |
| 16 Mar 2019 | Starcross Steamer at Starcross (Monohull dinghies) | |
| 17 Mar 2019 | Marlow Ropes Tipsy Icicle Series - Week 11 at Leigh & Lowton (Monohull dinghies) | |
| 23 Mar 2019 | Noble Marine Travellers Trophy (TT) at Cotswold (Supernova) | |
| 24-25 Mar 2019 | Southern Traveller at Bewl Sailing Association (Flying Fifteen) | |
| 24 Mar 2019 | IRC GBR Inland Championship at Windermere Cruising Association (IRC yachts and IRC yachts) | |
| 24 Mar 2019 | Windermere Winter Series at Windermere Cruising Association (Sonata and SB20) | |
| 24 Mar 2019 | Exmore Ales Beastie at Wimbleball (Monohull dinghies/multihulls) | |
| 25-31 Mar 2019 | BVI Spring Regatta at Nanny Cay, Tortola (IRC) | |
| 30 Mar 2019 | Torbay Tornado pursuit&sprints at Royal Torbay (Monohull dinghies/multihulls) | |
| 31 Mar 2019 | RNLI Open Handicap Trophy at Leigh & Lowton (Monohull dinghies) | |
| 6 Apr 2019 | Seminar at Chichester Cruiser Racing Club (Open to everyone) | |
| 6-7 Apr 2019 | Midland Area Championship / Open Meeting at Middle Nene (Enterprise) | |
| 6-7 Apr 2019 | Southern Area Championship at Datchet Water (Flying Fifteen) | |
| 6 Apr 2019 | Noble Marine Travellers Trophy (TT) at Bough Beech (Supernova) | |
| 7 Apr 2019 | Noble Marine Travellers Trophy (TT) at Bartley (Supernova) | |
| 10-14 Apr 2019 | 44Cup Porto Montenegro at Montenegro (RC44) | |
| 13-14 Apr 2019 | Lakeland Grand Prix at Royal Windermere (Flying Fifteen) | |
| 19-21 Apr 2019 | RORC Easter Challenge at Royal Ocean Racing Club (IRC and J70) | |
| 19 Apr 2019 | Class Coaching at Hunts (Supernova) | |
| 20 Apr 2019 | Noble Marine Travellers Trophy (TT) at Hunts (Supernova) | |
| 27 Apr - 3 May 2019 | Antigua Sailing Week at Antigua (IRC) | |
| 27-28 Apr 2019 | Keelboat Endeavour at Royal Corinthian, Burnham (IRC yachts and Sportsboats and IRC yachts) | |
| 4-5 May 2019 | Cervantes Trophy Race at Royal Ocean Racing Club (IRC) | |
| 5-6 May 2019 | Waples Wines Northern Traveller at Blackpool and Fleetwood (Flying Fifteen) | |
| 8 May 2019 | Antigua Bermuda Race at Antigua (IRC) | |
| 10-12 May 2019 | Vice Admiral's Cup at Royal Ocean Racing Club (Fast 40+, Performance 40, J/70, J/109, SB20, Quarter Ton, Diam 24 and other one design keelboats.) | |
| 11-12 May 2019 | Northern Area Championship & Lakeland GP at Ullswater (Flying Fifteen) | |
| 11-12 May 2019 | Tyler Trophy at Hayling Island (Solo) | |
| 18-19 May 2019 | Southern Traveller at Broxbourne (Flying Fifteen) | |
| 18 May 2019 | Noble Marine Travellers Trophy (TT) at Bolton (Supernova) | |
| 19 May 2019 | Noble Marine Travellers Trophy (TT) at Scammonden Water (Supernova) | |
| 25-26 May 2019 | Bulwark Trophy at Hayling Island (Flying Fifteen) | |
| 25-27 May 2019 | Southwestern Championships at Restronguet (Firefly) | |
| 25-27 May 2019 | Myth of Malham Race at Royal Ocean Racing Club (IRC and Class 40) | |
| 29 May - 2 Jun 2019 | Adris 44Cup at Croatia (RC44) | |
| 31 May - 1 Jun 2019 | North Sea Race at Royal Ocean Racing Club (IRC) | |
| 1-2 Jun 2019 | Inland Championship at Rutland (Flying Fifteen) | |
| 1 Jun 2019 | Noble Marine Travellers Trophy (TT) at Swarkstone (Supernova) | |
| 2 Jun 2019 | Noble Marine Travellers Trophy (TT) at Carsington (Supernova) | |
| 8-9 Jun 2019 | Open Meeting at Grafham Water (Flying Fifteen) | |
| 8-9 Jun 2019 | De Guingand Bowl Race at Royal Ocean Racing Club () | |
| 8-9 Jun 2019 | Solent Forts Race Weekend at Hayling Ferry (Monohull dinghies/multihulls with PY greater than 934) | |
| 14-16 Jun 2019 | Falmouth Classics at Falmouth (Classic Yachts) | |
| 15 Jun 2019 | Noble Marine Travellers Trophy (TT) at Attenborough (Supernova) | |
| 15-16 Jun 2019 | Scottish Championship at Loch Lomond (Flying Fifteen) | |
| 21-22 Jun 2019 | Morgan Cup Race at Royal Ocean Racing Club (IRC) | |
| 25 Jun 2019 | Transatlantic Race at Newport, USA to Cowes, UK (IRC) | |
| 28-30 Jun 2019 | International Regatta at UV Maccagno, ITA (RS Aero) | |
| 28-30 Jun 2019 | North American Championships at Columbia Gorge RA, OR, USA (RS Aero) | |
| 29-30 Jun 2019 | Waples Wines Northern Traveller at Dovestone (Flying Fifteen) | |
| 5-7 Jul 2019 | IRC National Championship at Royal Ocean Racing Club (IRC and Fast 40) | |
| 6-7 Jul 2019 | Open Meeting at Aldeburgh (Flying Fifteen) | |
| 9-13 Jul 2019 | 44Cup Marstrand at Marstrand, Sweden (RC44) | |
| 12 Jul 2019 | Class Coaching at Bowmoor (Supernova) | |
| 12-14 Jul 2019 | Cowes Dinard St Malo Race at Royal Ocean Racing Club () | |
| 13 Jul 2019 | Noble Marine Travellers Trophy (TT) at Bowmoor (Supernova) | |
| 20-21 Jul 2019 | UK Youth Championships at Rutland (RS Aero) | |
| 24-27 Jul 2019 | National Championship at Parkstone (Flying Fifteen) | |
| 24-28 Jul 2019 | UK National Championships at East Lothian (RS Aero) | |
| 27-28 Jul 2019 | Channel Race at Royal Ocean Racing Club (IRC and Class 40) | |
| 27-28 Jul 2019 | Telegraph Bowl at Royal Ocean Racing Club (XOD) | |
| 27 Jul 2019 | Noble Marine Travellers Trophy (TT) at Girton (Supernova) | |
| 3 Aug 2019 | Rolex Fastnet Race at Cowes to Plymouth (IRC) | |
| 3-8 Aug 2019 | Rolex Fastnet Race at Royal Ocean Racing Club (IRC and Class 40) | |
| 17-23 Aug 2019 | National Championships at Lyme Regis (Firefly) | |
| 18-23 Aug 2019 | European Championships at FV Malcesine, Lake Garda, Italy (RS Aero) | |
| 1-13 Sep 2019 | Pre-World & World Championship at National (Flying Fifteen) | |
| 6-7 Sep 2019 | Cherbourg Race at Royal Ocean Racing Club (IRC) | |
