Rubuta ci gaba don wannan sakin layi - Woollaston ya cancanci zuwa wasanni biyar a lokacin kakar 2013-14, wanda ya fi yawa a cikin kakar wasa daya a lokacin aikinsa. A Wuxi Classic ya doke Chen Zhe da Joel Walker duka 5<unk>2, kafin ya rasa 5<unk>2 ga Cao Yupeng a cikin 16 na karshe. Woollaston ya ci nasara a zagaye na farko na Australian Goldfields Open
, Gasar Duniya da kuma Jagoran Jamus. Ya ga Vinnie Calabrese da Alfie Burden tare da asarar tsari guda kawai don isa 32 na karshe na Welsh Open, inda ya kusa fitar da Ding Junhui amma ya rasa 4<unk>3. A cikin ƙaramar gasar Turai ta Turai, Ruhr Open, Woollaston ya fitar da zakaran duniya Ronnie O'Sullivan 4<unk>3 sannan ya farfado da Burden da Chris Norbury 4<unk>0, kafin ya rasa a cikin yanke shawara na karshe zuwa Stephen Maguire a wasan kusa da na karshe. Ya ci gaba da ci gaba a Antwerp Open ta hanyar doke Joel Walker a cikin kwata-kwata, amma O'Sullivan a wannan lokacin ya sami mafi kyawun Woollaston don cin nasara 4<unk>2 a wasan kusa da na karshe. Wadannan sakamakon sun taimaka masa zuwa matsayi na 20 a kan Dokar Merit don cancanta zuwa wasan karshe a shekara ta uku a jere. Woollaston ya doke Ding, mai nasara sau hudu a kan yawon shakatawa a wannan kakar, 4<unk>3 bayan ya kasance 3<unk>0 a baya don ci gaba zuwa 16 na ƙarshe na wani taron martaba a karo na biyu a wannan yakin, inda aka kawar da shi 4<unk>2 daga John Higgins.