Townhill, Fife born goalkeeper John “Jock” Gilfillan had played junior football since before the First World War for the likes of Woodend Juveniles in 1913 and Musselburgh Bruntonians in 1914, but joined Heart of Midlothian in 1921 from his local team Inverkeithing United, whom he’d joined after the end of the War, making his Scottish League debut against Leith Athletic that April.
However his early career for The Jambos wasn’t helped by his mistake in a Scottish Cup tie against Bo’ness that saw Hearts lose 3-2 in January 1923. He was subsequently loaned to East Stirlingshire in 1923 before returning to Hearts. A further loan spell to East Fife in 1926-27 saw him make an improbable appearance in the 1927 Scottish Cup Final where The Fifers lost 3-1 to Celtic at Hampden Park in front of 80,000 spectators. In total he made 93 senior appearances for The Jambos through to October 1928.
In November 1928 he joined First Division Portsmouth making his Football League debut in December against Cardiff City. He was ever present for five of the next seven seasons, missing only 6 League games, with the highlight Portsmouth’s appearances in the 1929 and 1934 FA Cup Finals at Wembley. Beaten 2-0 by Bolton Wanderers in 1929, a victory that sealed a hat-trick of 1920’s Cup wins for Bolton, they narrowly lost 2-1 in 1934 to Manchester City’s two late Fred Tilson goals.
Gilfillan was an ever present for Portsmouth in five of his nine seasons at Fratton Park, all in the First Division, and didn’t miss a match for four years between his Pompey debut and December 1932. After 360 appearances for Pompey, Gilfillan lost his place to Jimmy Strong and left Portsmouth to join Queens Park Rangers in the close season of 1937, making a further 24 appearances for Rangers and also a single appearance on loan to Clapton Orient – Gilfillan played for Clapton Orient against his registered club Queens Park Rangers on Thursday 11th November 1937 in a First Round Division Three Southern Section Cup game before 3,500 fans at Brisbane Road, Rangers winning 2-0. Orient had their two goalkeepers unavailable, Jacob Iceton on the injured list and Charlie Hillam, feeling unwell, had to go home, so Gilfillan was given permission to play against his Rangers teammates by Rangers management and the FA (he went back to Rangers the next day!) before retiring from professional football in the summer of 1938, after when he played non league football for Portsmouth Electricity.
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.”