Born in Colliers Wood, then part of the parish of Mitcham, Croydon, in 1878, and regularly played with his brother Mark for Tooting Graveney (a forerunner of Tooting Town) against Old Centrals.

In March 1898 he turned up to watch a South Western Cup game against Eagle Wanderers in Raynes Park, but as the referee failed to appear a friendly was played. When a player was injured he stepped in goal for the rest of the game.

After playing for Wingfield House (later to be renamed Nunhead) in 1903/04 and representing Surrey, he played twice against Old Centrals for Merton Manor at the end of that season, replacing his brother.

He joined Wimbledon as they took senior status at the start of the 1904/05. He was made captain for the 1905/06 season, and end of the season he married the rather delightfully named Primrose Belcher. He was again named captain for the 1906/07 season, but left halfway through the campaign.

Hugh was playing for Summerstown in 1907/08.

In 1909/10, working as a clerk for the Council, he was a regular for Wimbledon Corporation Employees, and was in goal for the merged Wimbledon Borough's first game the following season, his last recorded game being the prestige friendly against a Chelsea XI in November of 1911.

His brother, Mcivor Tindall Jackson, was also a goalkeeper, playing for Old Centrals' rivals, Merton Manor, and was a promising cricketer who played eleven first-class matches for Surrey between 1903 and 1907, alongside Wimbledon's Billy Davis