try in the Leeds Rhinos' 24-25 defeat to Hull FC, and another runners-up medal in the 2005 Super League Grand Final in the Leeds Rhinos' 6-15 defeat to the Bradford Bulls. Despite his success with the Leeds Rhinos, he declined a contract extension with the Leeds Rhinos and instead signed a 2-year contract with the Wigan Warriors starting in 2006. Wigan Warriors Calderwood made his début for the Wigan Warriors against the Catalans Dragons but it took him 3-months to get his first try for the Wigan Warriors which came against Castleford Tigers during May 2006. The Wigan Warriors spent most of 2006 struggling against relegation from the Super League but despite this he managed to form a good playing connection with the Wigan Warriors Chris Ashton. He did miss several months of 2006's Super League XI with an injury and finished the season with 6-tries. He represented England in the 2006 Federation Shield, scoring 2-tries in the opening match against France. 2002 saw him make his début for Yorkshire in the Origin match, in the 18-22 defeat and retained his place in 2003, scoring a sensational try at Odsal when Yorkshire defeated Lancashire 56–6. He also lifted the European Nations Cup with England, helping them reach the final with a hat trick against Russia in the qualifiers and then four against France in the final, with a man of the match performance and scored a hat trick of tries in the Wigan Warriors's epic 31–30 play-off victory over the Bradford Bulls on 21 September 2007 as the Warriors fought back from a 30–6 deficit but was forced off the field in the following match against Hull F.C. with a broken bone in his lower leg which forced him to miss the Wigan Warriors's last match of 2007's Super League XII against the Leeds Rhinos. The next season turned out to be his last one for the club. His form was mixed throughout the campaign and was signalled out for poor performances especially in the 10-46 defeat by local rivals St. Helens. Throughout his Wigan career he was criticised for not producing the form that gave him his name at the Leeds Rhinos, many fans thought that he had pace but was not giving everything into every match which began to have negative effect on his future at the club. He withdrew from the Scotland training squad for the 2008