Waterloo Cup 1944
| The Waterloo Cup of  1944 began on Wednesday 23rd February 1944. The entry conditions for the race required 64 subscribers to  subscribe their nomination at £25 each. The winner received £500 and a trophy  (valued at £100) donated by the Earl of Sefton. The runner-up received £200,  while the losing semi-finalists each received £50. The winner, Dutton Swordfish, was  owned by Mrs J A Dewar, wife of the director of Dewar's Distillers. The largest crowd for 20 years attended the event, although 90% of the crowd had to walk due to War transport restrictions. The winner was unique in that he had a broken tail. WATERLOO CUP WINNER:- DUTTON SWORDFISH (by Mellow Outlook out of Dutton Oak) The Plate saw Ann's Junior beat Bryn Tritoma The Purse saw Desert Drive (4/9) beat Castle in the Air |  | 
| 1. Loon 21/20 | Loon |  | ||||
| 2. Sale Ring | Countryman 8/15 | |||||
| 3. Signpost | Countryman 1/6 | |||||
| 4. Countryman 30/100 | Countryman | |||||
| 5. Fulcrum 4/5 | Fulcrum | |||||
| 6. Bilting Beaufort | Congress | |||||
| 7. Congress 1/7 | Congress 6/4 | |||||
| 8. Good Offer | Hylton | |||||
| 9. Valentine Castle 1/2 | Valentine Castle 2/7 | |||||
| 10. Holystone River | Valentine Castle | |||||
| 11. Glen Rover 2/1 | Glen Rover | |||||
| 12. Delightful Design | Hylton 5/1 | |||||
| 13. Odd Blend | Hylton 4/1 | |||||
| 14. Hylton 4/5 | Hylton 10/11 | |||||
| 15. Tennis Bank 13/8 | Tennis Bank | |||||
| 16. Jungle Rhythm | ||||||
| 17. Peerless Sight 4/6 | Jazz Record | |||||
| 18. Dew Jolly | Peerless Sight 1/3 | |||||
| 19. Right Back 4/9 | Peerless Sight | |||||
| 20. Noted Scotch | Right Back | |||||
| 21. Heddon Comet | Jazz Record 9/4 | |||||
| 22. Freedoms Flight 2/1 | Freedoms Flight | |||||
| 23. Desert Drive | Jazz Record 6/4 | |||||
| 24. Jazz Record 6/4 | Jazz Record 2/5 | |||||
| 25. Junior Corvette 2/5 | Jazz Record 4/9 | |||||
| 26. Fernbank | Junior Corvette 5/4 | |||||
| 27. Bryn Tritoma 10/11 | Junior Corvette | |||||
| 28. Joyful Rattle | Bryn Tritoma | |||||
| 29. Trade Test 1/3 | Trade Test | |||||
| 30. Longlands Oak | Trade Test 2/7 | |||||
| 31. Black Hills 4/7 | Trade Test 11/10 | |||||
| 32. Cons Castle | Black Hills | Dutton Swordfish | ||||
| 33. Lotus Lily 1/7 | ||||||
| 34. Smiling Bob | Lotus Lily 5/6 | |||||
| 35. Gala Soutar | Lotus Lily | |||||
| 36. Peaceful Scene 1/6 | Peaceful Scene | |||||
| 37. Cherry Ribbon 11/10 | Right Ahead | |||||
| 38. Good Opinion | Cherry Ribbon | |||||
| 39. Castle in the Air | Right Ahead 13/2 | |||||
| 40. Right Ahead 8/11 | Right Ahead 4/7 | |||||
| 41. Bryn Festival 1/7 | Dutton Swordfish 7/2 | |||||
| 42. Lightning Streak | Bryn Festival 2/9 | |||||
| 43. Ann's Junior 10/11 | Bryn Festival | |||||
| 44. Broughton Meddler | Ann's Junior | |||||
| 45. Ragwort | Dutton Swordfish 7/4 | |||||
| 46. Dutton Swordfish 8/13 | Dutton Swordfish 4/11 | |||||
| 47. Jorsebrook 13/8 | Dutton Swordfish 1/2 | |||||
| 48. Canada | Jorsebrook | |||||
| 49. Mundey 10/11 | Dutton Swordfish 4/9 | |||||
| 50. Crow's Sound | Mundey | |||||
| 51. Cyclopedia 4/6 | Cyclopedia | |||||
| 52. Nine Hundred | Cyclopedia 4/7 | |||||
| 53. Shamrock 6/5 | Lord Lieutentant 2/11 | |||||
| 54. Readers Advise | Shamrock | |||||
| 55. Lord Lieutenant 1/5 | Lord Lieutenant 1/4 | |||||
| 56. Heddon Storm | Lord Lieutenant 1/7 | |||||
| 57. Tall Tale 3/1 | Lord Lieutenant | |||||
| 58. Romford | Tall Tale | |||||
| 59. Brooch | Heddon Water 10/11 | |||||
| 60. Heddon Water 30/100 | Heddon Water 10/11 | |||||
| 61. Buff Rock 11/8 | Heddon Water | |||||
| 62. Law Lord | Buff Rock | |||||
| 63. Shan Van Voght 10/11 | Shan Van Voght | |||||
| 64. Joint Command | Shan Van Voght 4/6 | |||||
| I am very grateful to Gavin Purdon for forwarding the extract shown below from the diary of Mr Merryweather, of New Shildon, who had a keen interest in the Waterloo Cup. Robert William Merryweather (1890 – 1957), son of a railwayman, worked for the London & North Eastern Railways as a bricklayer's labourer at the Shildon Railway Wagon Works and kept a meticulous diary about coursing and horse racing. | 
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