 Nyorai kuenderera mberi kweiyi ndima - Kufungidzira kuti Sheringham achasiya United kwakawedzera nguva pfupi mushure mekunge mwaka wa1998 99 watanga, apo Dwight Yorke akatamira kuOld Trafford kubva kuAston Villa. Yorke pakarepo akaumba hukama hwakasimba naCole sezvo United yakaenderera mberi kuti iwanezve zita religi pazuva rekupedzisira remwaka. Mikana yaSheringham yechikwata chekutanga yaive shoma asi zvakadaro akakwanisa kuita zvakaringana kuoneka kuti akwanise kuwana menduru yemakwikwi pakupera kwemwaka pazera remakore makumi matatu nematatu aive ahwina mukombe wake wekutanga mukuru. Vhiki rimwe gare gare akauya achibva pabhenji revatambi kuti arove chibodzwa chekutanga cheUnited mukukunda 2-0 kweNewcastle United mufainari yeFA Cupkuchengetedza kaviri. Mazuva mana mushure mekukunda kweFA Cup, Sheringham akarova mutambo wakasarudzika-nguva yekuenzanisa neBayern Munich mumutambo weChampions League, mushure mekunge auya sechinotsiva pakutanga mumutambo. Pasara masekondi mashoma kuti mutambo upere, Ole Gunnar Solskjær akahwina zvibodzwa kubva kuSheringham, United ikahwina mukombe wePremier League, FA Cup neEuropean Cup naSheringham asina kuhwina mukombe mukuru mumakore ake gumi nemashanu achisiya Spurs iye zvino akahwina mukombe wese wepamusoro mumutambo weChirungu. 