Captain Frederick Howard Jackson of 2nd Battalion Connaught Rangers, was the son of Captain Jackson and his wife of Oakham and went to Oakham School. He became a regular soldier, promoted to Captain in 1905. He died on 28 October 1914 in the fighting around Ypres and is remembered on Panel 42 of the Menin Gate. He is also remembered in Oakham School Chapel, but not on the town's war memorial. It was Captain Jackson's battalion that came to the attention of a Daily Mail correspondent, George Curnock, when he heard them singing It's a Long Way to Tipperary in Boulogne 1914. He wrote: "A company of the 2nd Battalion Connaught Rangers passed us singing, with a note of strange pathos in their rich Irish voices, a song I had never heard before."

It's a long way to Tipperary, It's a long way to go, It's a long way to Tipperary, To the sweetest girl I know, Goodbye Piccadilly! Farewell Leicester Square! It's a long, long way to Tipperary, But my heart's right there!