He was one of the "Famous Five", the Hibernian forward line during the late 1940s and early 1950s, along with Bobby Johnstone, Gordon Smith, Eddie Turnbull, and Willie Ormond.
[4] Reilly was a fringe player in the 1947–48 season as Hibs won the league championship, playing in insufficient games to earn a winners' medal.
[4] It was reported that Reilly and Johnny Aitkenhead might be loaned to Edinburgh derby rivals Hearts, who were battling against relegation that season.
[4] That season also provided a major disappointment in Reilly's international career, as Scotland qualified for the 1950 FIFA World Cup, but the SFA refused to send the team to Brazil because they had failed to win the 1950 British Home Championship.
Hibs finished second to Rangers in 1953 and the club's fortunes started to go into decline, although Reilly continued to perform well.
[4] Reilly almost quit football after a row with Hibernian after manager Hugh Shaw refused him a testimonial match.
He also boasts an international strike rate of 61%, greater than that of Kenny Dalglish, Denis Law and Joe Jordan, and second only to that of Hughie Gallacher amongst those capped more than 15 times.