 Nyora kupfuurira kweiyi ndima - Pakupera kwemwaka wa 200001, kondirakiti yaSheringham yemakore mana kuOld Trafford yakapera. Akanga achitarisana nemakwikwi akasimba kupfuura nakare kose nokuda kwenzvimbo dziri mberi, zvikurukuru kubva kumurwi mutsva weUnited Dutch Ruud van Nistelrooy. Akaramba chibvumirano cheUnited chemwedzi gumi nemaviri uye akadzokera kuTottenham pakutengeswa kwemahara semumwe wevatambi vatsva vemaneja Glenn Hoddle. Mumwaka wake wokutanga shure, Sheringham akabatsira Tottenham kusvika kunzvimbo yechipfumbamwe, yepamusoro yekirabhu mumakore matanhatu, uye kusvika kumagumo eLigi Cupuko vakarasikirwa ne2 ku1 kuBlackburn Rovers, naSheringham achiiswa pasi munharaunda yechirango muminiti yekupedzisira nokuda kwezvaaifunga kuti yaiva chirango. 2002-03 yakaunza zvakafanana pakati petafura yekupedzisa, kunyangwe Tottenham yakanga yatungamira iyo Premiership mitambo mitatu mumwaka. Sheringham akaita mitambo makumi masere mumakwikwi ese eTottenham munguva ino, achihwina zvibodzwa makumi maviri nezvitanhatu. 