 Nyorai kuenderera kweiyi ndima - NaFranck Queudrue chete anokwanisa kutamba kuruboshwe-kumashure, Steve McClaren akadzosa Taylor kubva kuBradford City mwaka unotevera wa2005-06, kwaakange afadza pachikwereti. Taylor akaita Middlesbrough kutanga kwake, kutanga mutambo uye akatamba maminitsi 61 asati achitsiviwa, mukurasikirwa ne7-0 neArsenal musi wa14 Ndira 2006. Mwedzi mumwe gare gare musi wa 23 February 2006. Akaita UEFA Cup yake yekutanga kurwisa VfB Stuttgart mumutambo wechipiri weRound ye32, mukurasikirwa ne10, asi akaona kirabhu ichienda kumutambo unotevera pachinangwa chekunze. Kubvira paakatanga kutamba kirabhu, akazviwana ari mukati uye kunze kweiyo yekutanga line-up yeiyo yasara ye2005-06 mwaka. Munguva yemwaka wa2005-06, Boro yakasvika kuma semi fainari eFA Cup uye 2006 UEFA Cup Final.. Taylor akatamba mumitambo yakati wandei yePremier League uye FA Cup semi-fainari kuchengetedza Queudrue yeEFAFA Cup tie neSevilla. Chimiro chake chinoshamisa chakaratidzira kuti akanga asina rombo rakanaka kupotsa nzvimbo yokutanga kurwisana naSevilla. Pakupera kwemwaka wa2005-06, akaita makwikwi makumi maviri mumakwikwi ese. 