On 1 August 2000, Whittaker joined the likes of Kenny Miller and Derek Riordan in signing for Hibernian from Hutchison Vale Boys Club. He made his debut against St. Johnstone in a 1–0 win on 12 May 2002. In the 2002-03 season, he went on to make further six first-team appearances before finally become a regular starter the season after. Due to Whittaker lacking a defined position his form suffered as he was deployed at right-back and across the midfield under Bobby Williamson. He scored his first career goal against Partick Thistle in a 3–2 win on 3 January 2004. He was an unused subsitutite when Hibernian lost the 2004 Scottish League Cup Final.
The arrival of Tony Mowbray later that year saw Whittaker confirmed in the team's right back role, and with this new certainty, he flourished, becoming a regular in the Scotland Under–21 team and helping Hibernian to a third place league finish. Whittaker was a regular in the Hibs teams of both Mowbray and John...... Read More