Donnybrook, Dublin born goalkeeper Matt “Gunner” or “Ginger” Reilly had only played Gaelic football before leaving Ireland behind to serve in the army. He took to the association game while in Glasgow, playing as goalkeeper with junior side Glasgow Benburb, but it was while playing with The Royal Artillery (based in Portsmouth) that he really came to prominence, playing in their 1896 Amateur Cup Final defeat by Bishop Auckland when Reilly was voted “Man of the Match” when he kept the score down to a 1-0 defeat, as well as playing in two Army Cup Finals with The Royal Artillery. He became a key member of the Royal Artillery side and helped them rise to join the Second Division of the Southern League in 1897 and win the Division title at the end of the 1897-98 season. The R.A. were less successful in their first season in the top division, finishing at the foot of the table, and subsequently the club folded, with Reilly making 42 Southern League appearances.
He represented The Army, Hampshire and Forfarshire and had first played Southern League football on loan with Southampton St Mary’s in December 1895, playing twice for The Saints when he replaced Tom Cain and both matches (against Reading and Royal Ordnance) ended in 5-0 victories. and also having a loan spell with Southampton based Freemantle, before leaving The Services and taking to the professional game with the fledgling Portsmouth, joining them in May 1899. Pompey quickly grew to become one of the dominant forces of the Southern League, finishing third, second, then as Champions in 1901-02, then third and fourth between 1900 to 1904. Reilly was recognised for his form with selection for Ireland on two occasions, both narrow defeats by England, his debut coming in a 2-0 defeat at Lansdowne Road, Dublin in March 1900, and his other cap a 1-0 defeat at The Balmoral Showgrounds, Belfast in March 1902.
During a match against Swindon on 30th January 1904 he was hit by a projectile thrown from the crowd and punched a spectator, subsequently he served a two week suspension. Having played 159 Southern League and FA Cup matches for Portsmouth, Reilly moved to Scottish League Dundee in the 1904 close season but played only 3 times for them before playing the only Football League matches of his career with First Division Notts County, signing for them in June 1905. He made an inauspicious debut in a 3-0 defeat at Stoke that September and lost his place mid-season to Albert Iremonger (who at 6’ 5½“ was to become a Magpies legend) after 16 appearances. Still, Reilly was recognised as a valuable asset and it took a £100 bid from Tottenham Hotspur to take him back to the Southern League in October 1906, where he played 26 Southern League and FA Cup games during his single season at White Hart Lane.
In August 1907 Reilly returned to Dublin to play for Shelbourne. He played for The Shels in 1908 Irish Cup Final, but finished on the losing side to Dublin rivals, Bohemians, retiring in 1909.
He remained fondly remembered at Fratton Park and was amongst the guests who celebrated Portsmouth’s fiftieth anniversary in 1948.