He was a first-class cricketer for Victoria, footballer for Essendon and Melbourne in the Victorian Football League (VFL), as well as a tennis player at the Australasian Championships (now known as the Australian Open).

[2] After managing only five appearances for Essendon during his time at the club in 1899 and 1900, Rainey crossed to Melbourne where he had more success.

He played a full season in 1902, including Melbourne's semi final loss to his old club, and kicked 17 goals.

Rainey finished his football career with 23 VFL games and 20 goals.

He put in a good performance in the second of those matches, in 1905, scoring an unbeaten 60 and taking 6/46 in Tasmania's second innings.