 Ramba uchiverenga ndima iyi - Willoughby akaberekerwa muSpringburn, kuGlasgow, uye akadzidza paPetershill Primary School uye paColston Junior Secondary School, zvose zviri munzvimbo yeSpringburn. Akatamba nhabvu yevechidiki nechikwata chake chemuno chevakomana veBrigade, uyezve neDrumchapel Amateurs asati atanga basa rake neRangers semwana wechikoro achisaina aine makore gumi nemashanu muna 1959. Akazosaina mazwi ehunyanzvi neRangers muna 1961. Akahwina mu1963 Scottish League Cup Final kukunda Morton, asi akasiyiwa kubva ku1967 European Cup Winners Cup Finalchikwata chakashamisa vakawanda, naRoger Hynd akasarudzwa, pasinei nokuti Willoughby akanga arova zvibodzwa 17 mumitambo 14 mumwedzi mitatu yakanga yapfuura. 