Robert Middleby (born 9 August 1975) is an Australian former football player who as a right-back or right midfielder.

He saw little game time under coach Pierre Littbarski in his first season at the club, playing only 212 minutes in 16 appearances despite scoring in Sydney FC's 3–1 victory against New Zealand Knights early in the campaign.

Despite missing part of the season with a broken collarbone after a controversial off-the-ball incident involving Melbourne Victory FC defender Adrian Leijer,[2][3] Middleby was voted Sydney FC Players' Player of the Year for the season.

[4] Middleby accidentally broke David Beckham's rib, when Sydney FC played the Los Angeles Galaxy at ANZ Stadium in November 2007.

On 11 February 2010, he announced his retirement from professional football at the end of the 2009–10 season[5] Middleby played his last game against Gold Coast United FC, which North Queensland won 2–1.