Madeley, Shropshire born outside right Dickie Guy began his senior football career on the books of Manchester City in the 1902-03 season, but he didn’t feature in their first team and was signed by newly elected Second Division club Bradford City in the 1903 close season, making his Football League debut in their inaugural League fixture in a defeat at Grimsby Town at the start of September. His second match was in slightly happier circumstances, when he had the honour of scoring the first goal ever scored by Bradford City in the Football League, coming on 5th September 1903 in a 3-1 defeat by Gainsborough Trinity at Valley Parade. According to The Bradford Daily Argus, the goal was greeted with “a shout which awoke babies on the distant hillsides of Bolton and Eccleshill”. However after 2 goals in 8 matches for The Bantams he lost his place in October and played in only one further FA Cup tie the following month.
After a spell in non league football with Hastings & St Leonards in 1907, he returned to Football League action when he signed for Second Division club Leeds City in May 1908 where he made his Peacocks debut in the third match of the season, in a 2-0 home win over Hull City on 12th September 1908. He laid on one of the goals for Adam Bowman with a fine cross and, according to Sportsman in The Leeds Mercury, it was “an exceedingly promising debut”.
Probably his best performance for City came in a 5-2 victory over Wolverhampton Wanderers at Elland Road in front of 14,000 on 12th December 1908. Linesman in The Leeds Mercury had this to say: “It was indeed a fortunate circumstance that led to the re-inclusion of Guy. Guy had already figured in the team without accomplishing anything brilliant, but he seized his opportunity on Saturday with both hands (and feet), and Richard Guy, as featured in Bradford City’s first handbook in 1903, when he scored the Bantams’ first goal in League football showed so much dash and skill as to make himself the most outstanding forward on the field. So big a part did he play that he had a large share in all the five goals scored for Leeds City. The three that were got in the first half were almost the direct result of his centres. In view of Guy’s performance, the problems of the Leeds City right wing would appear to be solved, for the fair haired outside-right undoubtedly earned his place, and it is to be hoped he will keep it”, although he generally suffered from inconsistency and played only a single season at Elland Road during which he scored 4 goals in 22 appearances.
He moved on to Southern League club Portsmouth at the start of the 1909-10 season, but only had a single season at Fratton Park. He later rejoined Hastings & St Leonards in 1910 for £25. Guy enlisted in the Special Reserve in March 1908 and during the First World War he served for a year on the Western Front in The Duke of Lancaster’s Own Yeomanry.