Born in Fairfield, Derbyshire, Kitchen was an outstanding sportsman and became a professional golfer at the age of 14. He also played cricket and for a time worked as a coach at Dulwich College. He eventually decided to concentrate on football and, after a period with his local club, Buxton, playing in The Combination, he joined Stockport County, then playing in the Lancashire League.
After a year at Stockport, he move up to the Football League, joining Everton in 1898 as cover for Scottish international, Willie Muir. Kitchen made his debut on 14 January 1899, in a 2–0 victory over Preston North End. It was not until October 1901 that he became Everton's first-choice custodian, following Muir's departure, helping Everton to reach the runners-up position in the First Division at the end of the 1901–02 season. He retained his place in the side until the arrival of Irish international Billy Scott in the summer of 1904.
After a season spent in the reserves, Kitchen was transferred in the summer of 1905 to West Ham United of the Southern League, as replacement for Matt Kingsley who had been dropped following a sending-off in March. At West Ham, Kitchen became the club's penalty taker and became the first-ever goalkeeper to score on his debut with a penalty against Swindon Town on 2 September 1905. Over the next six years, Kitchen rarely missed a match for the Hammers before losing his place to John Geggus in 1911, leading to another season in the reserves. In his seven-year span at West Ham, Kitchen made 205 appearances in the Southern League or F.A. Cup, scoring six goals.
In October 1912, he was rescued from West Ham's reserves by Southampton's new trainer, Jimmy McIntyre (who acted as "manager" under "secretary" Ernest Arnfield). Described at the time as "having the perfect build for goalkeeping", Kitchen was past his prime by the time he signed for the "Saints", but immediately replaced Bill Knight in goal, making his debut in a 0–0 draw with Coventry City on 26 October 1912. Kitchen's experience soon installed a sense of confidence into a defence that had been struggling, and Saints won five of his first ten games in goal, having only won once in the previous two months.