Raybould established himself quite late on the League scene after playing with a string of amateur sides. He was 24-years-old when he scored ten goals in 13 games in half a season for second division New Brighton Tower, before stardom at neighbours Liverpool. Raybould was the first player to score 100 League goals for Liverpool, a feat he achieved in 162 first and second division matches between 20 January 1900 and 9 December 1905. Raybould was top-scorer with 17 when Liverpool won the League Championship for the first time in 1901 but his most prolific period came two years later when he grabbed 32 goals from 34 League and cup games! His abilities were obvious to everyone. “He is a dangerous player when in possession, and backs who make mistakes might as well concede a goal straight away,” the local press reported admiringly.
 
After becoming the first Liverpool player to score 30 goals in one season in 1903 Raybould got himself in trouble with the football authorities by agreeing to 'financial inducements' to sign for southern league Portsmouth along with teammates John Glover and William Goldie. The Southern league was the dominant competition in Southern and Central England outside the Football League. When The Football League was founded in 1888 it was based entirely in the North and Midlands with the establishment of County Football Associations in the South being firmly opposed to professionalism. Portsmouth tried to use lack of regulations of transfers between the leagues to their advantage, but their approach was deemed as illegal and Raybould was suspended for seven months for agreeing to sign for Pompey. He was also given a lifetime ban on ever signing for the south-coast side. His absence proved significant as Liverpool slumped from fifth place a year before to relegation candidates. During the enforced break Raybould was very successful in quarter of a mile professional sprints in the Midlands and is said to have run 120 yards (110 meters) in just over 11 seconds. His ban lasted until 31 December 1903, but he seemed to have been forgiven for wishing to move as he was selected for the first team straight away in January. But, even Raybould's four goals from 15 games towards the end of the season could not prevent the dreaded drop into the Second Division.

Raybould was a strong and powerful striker with a wonderful turn of speed, good ball control and was praised for his daring rushes up-field and judicious distribution of play to the wingers, but first and foremost, his deadly scoring capacity. He was moved from centre-forward to left wing in the Second Division and struggled to make an impression in the opening matches for which he was greatly criticized. At the time he suffered more abuse from his own fans than any other player, as they had expected him always to score goals. In the end Raybould came good and scored 19 League goals as the club made an immediate return to the First Division. He made a significant contribution when the First Division was won just a year later by scoring 11 goals in 25 matches. The last of Raybould's 211 League appearances for Liverpool came on the final day of the 1906/07 season at home to Sheffield United and he marked the occasion in typical fashion with a goal, the last of the 130 he scored for the club. Even though for being such a sensational goalscorer for Liverpool he never played for the English national team, but featured three times for the Football League XI playing the Scottish League XI.

Thirty-two-year-old Raybould left Liverpool in 1907 for first division Sunderland. He scored ten goals in 27 League games in the 1907/08 season keeping Sunderland just above the relegation places. After only one season he went to fellow first division team Woolwich Arsenal and scored six goals in 26 League games for sixth-placed future Gunners before going down a couple of divisions to guide Chesterfield Town to the Midland championship, scoring 14 goals in 47 games in his two years there. A true goalscoring legend!