next two months, due to illness and competitions. In between the absent, Caldwell made his first UEFA Champions League start against Bayer Leverkusen, as the club won 3–1 on 26 February 2003. He later made four more appearances later in the 2002–03 season and contributed to the club's UEFA Champions League qualification to next season. In total, Caldwell made seventeen appearances and scoring once in all competitions. Local newspaper Evening Chronicle said his involvement in the first team "deserves credit for his unsung contribution" With his contract expiring at the end of the 2002–03 season, Caldwell said about his future, saying: "I've been in a worse position at this club. I'm not expecting anything at the moment. If the club wants me to stay, I'll be delighted, but I'm 22 and I don't want to spend my time in the reserves. I want to be playing for my country and I won't be doing that if I'm in the reserves." Newcastle United offered a him a new contract, but he rejected it, with clubs like Rangers, Sunderland and Sporting CP were interested in signing him. With an imminent departure from Newcastle United, the club demanded a £750,000 compensation. But in an unexpected turn of an event, it was announced on 19 June 2003 that Caldwell signed a one–year contract extension with the club, having previously rejected the one before, describing it as an "insult". It wasn't until on 15 October 2003 when Caldwell made his first appearance of the 2003–04 season, coming on as a 78th-minute substitute, in a 1–0 win against NAC Breda in the UEFA Cup, a win that saw Newcastle United through to the next round of the tournament following a 6–0 win on aggregate. He then made three more appearances for the club in the first half of the season. Manager Robson praised his performance in the last two matches. However, Caldwell continued to found his first team opportunities limited, due to competitions and his own injury concern. Because of this, Caldwell wanted to leave Newcastle United if he was not given first team football at the club. At one point, Caldwell was expected to leave Newcastle United on loan but Manager Robson blocked any attempts following an injury of Jonathan Woodgate. After Newcastle United recalled him due to an injury of Woodgate and Griffin, he made his appearances for the club since leaving, coming against