Pierre Littbarski
Middleby 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. He gained favour, though, under Littbarski's replacement Terry Butcher and was a regular starter in the 2006–07 season. Despite missing part of the season with a broken collarbone after a controversial off-the-ball incident involving Melbourne Victory defender Adrian Leijer, Middleby was voted Sydney FC Players' Player of the Year for the season.