With only Franck Queudrue able to play at left-back, Steve McClaren brought Taylor back from Bradford City the following 2005–06 season, where he had impressed on loan. Taylor made his Middlesbrough debut, starting a match and played 61 minutes before being substituted, in a 7–0 loss against Arsenal on 14 January 2006. A month later on 23 February 2006. He made his UEFA Cup debut against VfB Stuttgart in the second round of the Round of 32, in a 1–0 loss, but saw the club through to the next round on away goal. Since making his debut for the club, he found himself in and out of the starting line–up for the rest of the 2005–06 season. During the 2005–06 season, Boro reached the FA Cup semi-final and the 2006 UEFA Cup Final. Taylor played in several Premier League matches and the FA Cup semi-final to save Queudrue for the UEFA Cup tie with Sevilla. His impressive form meant he was unlucky to miss out on a starting place against Sevilla. At the end of the 2005–06 season, he made twenty appearances in all competitions.