Chester born outside left Herbert Lipsham began by playing in his home city with St Oswald’s in 1895 before making his debut for Chester in the 1895-96 season.After a spell with Rock Ferry in 1897, Lipsham joined Crewe Alexandra in 1898 as a professional and was an immediate success, his first senior appearance coming in an FA Cup tie at Glossop in November 1898. So much did he impress that First Division clubs Derby County, Notts County and Sheffield United all showed an immediate interest in him.
Crewe were not anxious to part with him, but a substantial offer induced them to transfer him to Sheffield United in February 1900. After that, he was an invaluable member of the successful Blades team of that period. A quiet and unassuming young man, he was famous for his hard-hit crosses, which produced a lot of goals for his central strikers. Having established himself in the Blades team in 1900, Lipsham played in the 1901 FA Cup Final defeat to Tottenham Hotspur in 1901, but a year later was in the successful FA Cup Final team when Sheffield United beat Southampton 2-1 in a replay on 26th April 1902 at The Crystal Palace.
He made his England debut in a 0-0 draw with Wales at Wrexham in March 1902 in what would prove his only England cap, although he also played twice for The Football League and later in his career twice represented The Southern League.
He played a total of nine seasons at Bramall Lane but eventually lost his place in February 1908, and after 34 goals in 259 appearances he moved to Second Division Fulham in April 1908, staying two seasons at Craven Cottage and scoring 5 goals in 59 appearances before joining Southern League Millwall in the 1910 close season. Lipsham was appointed player-manager at Millwall Athletic in May 1911, retaining the position until the end of the First World War in 1918, scoring 13 goals in 85 appearances for The Lions. He was later manager of Northfleet from 1922 to 1923.
His younger brother Jack played for Chester, Liverpool and Wrexham. Two other brothers also played for Chester.