Career
He joined Hearts from his local team Inverkeithing United, and played for Hearts in a 1922-1923 Scottish Cup tie against Bo"ness. He was later loaned to East Fife, and played for them in the 1926-1927 Scottish Cup final against Celtic. Gilfillan moved to play in England with Portsmouth of the Football League in 1928.
He was to go on to make 359 senior appearances with the south coast club, including playing for them in the 1929 and 1934 Finals.
In his nine seasons with the club he kept 107 clean sheets in 330 League matches. He eventually left Portsmouth to play for Queens Park Rangers, where he made 21 League appearances, and he then had a short loan spell with Clapton Orient, although he did not play a league game for them.
He played for Clapton Orient against his registered club Queens Park Rangers on Thursday 11 November 1937 in a First Round Tie of the Southern Section Cup. The score Orient 0 QPR 2 before 3500 fans.
Orient had goakeepers" Charlie Hillam feeling sick and Jacob Iceton on the injured list, so permission was given by the FA for him to play for Orient.
He went back to Rangers the next day. (Source: Neilson Kaufman, historian Leyton Orient Football Club. In April 2009, he was included in a Times list of the Top 50 Portsmouth players of all time, and was described as being "one of the finest keepers in the club’s history with excellent positioning and agility the key to his success.".
