 Sherwood akatanga basa rake rekurairidza kuTottenham Hotspur, achifambira mberi kubva kumubatsiri wekutanga-timu murairidzi kuenda kumaneja mumakore mashanu, ndokuzotungamira kirabhu kubva muna Zvita 2013 kusvika pakudzingwa kwake muna Chivabvu 2014. Akatangazve basa rake rekutungamira kuAston Villa muna Kukadzi 2015, achivaendesa kumakwikwi eFA Cup mwaka iwoyouye akavadzivirira pakudzingwa muPremier League, kusvikira vadzingwa basa muna October 2015. Sherwood aiva mutungamiri wenhabvu kuSwindon Town kubva munaNovember 2016 kusvika munaJune 2017. 