There is no consensus as to the exact origin of the Cavalier King Charles Spaniel.  However, they can definitely be traced back to the 16th century in England.  The Cavalier as we know the breed today is a direct descendent of the small Toy Spaniels seen in paintings during the 16th, 17th and 18th centuries.  These early spaniels, as documented in paintings,  had longer, pointier snouts and thinner-boned limbs than the Cavalier King Charles Spaniel. 

These small Toy Spaniels were favorites of the royal family and aristocracy, and were commonly referred to as "Spaniel Gentle or Comforter Spaniel."  These small dogs took on many roles: the companion, lap warmer, foot warmer, and more.  Some even thought that the Toy Spaniel could ward away flees.

During Tudor times, Toy Spaniels were quite common as ladies' pets.  It was under the Stuarts that they were given the royal title of King Charles Spaniels.  However, the King Charles Spaniel is most associated with King Charles II, who they were named after.  Charles II was crowned King of England in 1660, upon his return from exile in France.  His reign spanned from 1660-1685.  The breed gained prominence during the reign of King Charles II because he had a large number of the King Charles Spaniels that followed him everywhere.  Charles II wrote a decree that the King Charles Spaniel should be accepted in any public place, even in the Houses of Parliament where animals were not usually allowed.  Charles II was known as the Cavalier King and his first parliament was known as the Cavalier Parliament.  His brother, James II succeeded the thrown and was crowned King of England in 1685.  James II was also partial to the small King Charles Spaniel.  The King Charles Spaniel maintained its “royal status” until the end of James II’s reign.

Queen Mary I and William the Orange took the throne in 1689.  They favored breeds such as the short-nosed Pug and Japanese Chin. The characteristics of the short-nosed Pug and Japanese Chin were passed down to the existing court's spaniels by breeding these dogs to King Charles Spaniels.  This breeding resulted in a transformation of the King Charles Spaniel.   The King Charles Spaniel became smaller, with a dome-shaped head, low-set ears and a short muzzle with a pushed-up, laid back nose.  This new Spaniel was also known as the King Charles Spaniel or English Toy Spaniel, with its more domed skull and shorter nose.  Consequently the longer nosed “original type” King Charles Spaniel seen during the Charles II reign were all but extinct by the mid 1920s.  

In early 1920's, an American named Roswell Eldridge, traveled to England, and visited the Crufts Dog Show.  He did not see any of the “long nosed” Spaniels that he remembered from his boyhood, the Spaniels similar to the ones favored by King Charles II.  Not only were these “long nosed” Spaniels not at the Crufts Dog Show, he could not find any of these dogs in England.  Not willing to give up, he presented a challenge to the King Charles Spaniel breeders, placing an advertisement in the catalogue for the Crufts show in 1926.  He offered prize money in the amount of £25 (approximately $2,500.00 American, in today's currency) for both the first place dog and bitch of the “old type” King Charles Spaniel exhibited at Crufts each year for three years, 1926-1929.  The challenge was later extended for two more years.  The ad read as follows: 

'Blenheim Spaniels of the Old Type, as shown in pictures
of Charles II's time, long face, no stop, flat skull, not inclined to be domed with spot in centre of skull.  First
prize of £25 in Class 947 and 948 are given by Roswell Eldridge Esq., of New York, USA.  Prizes go to nearest to type required.'

This challenge was presented to the breeders to see if they could reproduce the “original type” King Charles Spaniel.  The English King Charles Spaniel breeders were not very interested in the challenge.  They spent many years breeding to produce the new flat faced King Charles Spaniel, and had no interest in reproducing the “original type” King Charles Spaniel with the longer nose.  In fact, breeders participating in this contest suffered much ridicule in their attempt to revive the breed back to its original form.        

In the first year only a couple of entries were made.   Interest soon began to grow, and a small core of enthusiasts banded together to work to recreate the “original type” King Charles Spaniels.  One of the leading pioneers in reproducing the “original type” King Charles Spaniel was Mrs. Hewitt Pitt.  Mrs. Pitt was a well-known breeder of Chow Chows.  In 1924 she purchased a blenheim King Charles Spaniel bitch puppy as a pet for her mother.  Mrs. Pitt was urged to show this dog at Crufts in Mr. Eldridge's sponsored class.  Mrs. Pitt entered the bitch, named Waif Julia, and won the class.  Mrs. Pitt became interested in the possibilities of breeding this "original type" King Charles Spaniel.  Thus, the "Ttiweh" prefix (Hewitt reversed) came into being, and the seed of the idea of a Cavalier Club was first sown.   

In 1928 a dog owned by Miss Mostyn Walker, Ann's Son, was awarded the £25 prize. (Unfortunately Roswell Eldridge died in 1928 at age 70, only a month before Crufts, so he never saw the results of his challenge prizes.)  It was in the same year, at the Crufts show, that a small group of breeders of “original type” King Charles Spaniels united and a breed club was formed.  The name Cavalier King Charles Spaniel was chosen for the new breed.  The addition of the word Cavalier was used to distinguish the new breed from the short nosed King Charles Spaniel.  It was very important that the association with the name King Charles Spaniel be kept, as most breeders bred back to the original type by way of the long-faced “rejects” from the kennels of the King Charles Spaniel breeders. Some of the dogs threw back to the long-faced variety very quickly. 

The breed standard was also formed at this first Cavalier King Charles Spaniel club meeting in 1928. Ann’s Son was brought to the meeting, as a live example of what the Cavalier King Charles Spaniel should look like. Club members also brought in pictures of Toy Spaniels depicted in paintings of the old masters.  The breed standard provided that there was to be no trimming of a Cavalier.  The founding club members wanted a dog in its natural shape with no alterations by trimming or other means.

Mrs. Pitt went on to impact the "reestablishment" of the Cavalier King Charles Spaniel through her dedication to the breed and her high standards of perfection.  Mrs. Pitt's "Ttiweh" prefix is found in the ancestry of Cavaliers all over the world.  The six foundation dogs of this reconstructed Cavalier King Charles Spaniel were Ann's Son, his litter brother Wizbang Timothy, Carlo of Ttiweh, Duce of Braemore, Kobba of Kuranda and Aristide of Ttiweh. 

After a period of hiatus during World War II, dog shows resumed.  In 1945 the English Kennel Club granted separate registration status to the “Cavalier Spaniels.”  The Club later requested that the title be changed to the "Cavalier King Charles Spaniel" and this was accepted by the Kennel Club.

In 1946, the breed was awarded championship status, and on August 29, 1946, the very first Cavalier specialty show was held on the grounds of Stratford On Avon School of Drama, at the home of Mrs. L Hitching (Avoncliffe). 41 Cavaliers entered; Best in Show, and Bitch Challenge Certificate, was awarded to a Blenheim bitch "Belinda of Saxham.”  Belinda of Saxham, was owned by Mrs. Katie Eldred.  Aristide of Ttiweh was the sire of Belinda of Saxham.  The Dog Challenge Certificate was awarded to "Daywell Roger.”  Daywell Roger was owned by Mrs. Pitt’s daughter, Jane Bowdler.  In 1948 Daywell Roger became the first English Cavalier King Charles Spaniel Champion.  Ch. Daywell Roger was a very widely used stud, and was a major contributor to the development of the breed in the middle of the Century.