Educated at the King's School, Chester Lipsham was a goal-scoring outside left . He began by playing in his home city with Chester St Oswald's before making his debut for Chester in the 1895–96 season. He had been one of four brothers to play for Chester, with the others including Jack who went on to play for Liverpool .
After a spell with Rockferry, Lipsham joined Crewe Alexandra in the 1898–99 season as a professional and was an immediate success. So much so that Derby County , Notts County and Sheffield United showed an immediate interest in him.
Crewe weren't anxious to part with him, but a substantial offer induced them to transfer him to Sheffield United in 1900. After that, he had been an invaluable member of the successful Blades team of that period. A quiet, unassuming and well-behaved young man, he had been famous for his hard-hit crosses, which produced a lot of goals for his central strikers. Lipsham played in the successful FA Cup Final team when Sheffield United beat Southampton 2–1 in a replay on 26 April 1902. He moved to Fulham in 1908.
Lipsham was appointed manager at Millwall on 4 May 1911, retaining the position until the First World War.
He additionally had a tobacconist shop at 142 Bramall Lane.