Ledley's first goal of the 2005–06 season came in a 2–1 League Cup victory over Macclesfield Town. He scored the equaliser after the League Two side had taken the lead. A month later, on 18 October, he scored in Cardiff's 2–2 draw against Preston North End. Four days later Cardiff beat Crewe Alexandra 6–1, with Ledley scoring the second to put them 2–1 up shortly after half time. Cardiff had been tipped for relegation at the start of the season but this victory put them on the verge of the play-off places. Ledley's fourth goal of the season came in a 2–1 victory over Southampton on 31 December.