Woollaston akakwanisa kupinda mumakwikwi mashanu mumwaka wa2013/14, zvinova ndizvo zvaakawana mumwaka mumwe chete pabasa rake. PaWuxi Classic akakunda Chen Zhe naJoel Walker vese 5<unk>2, asati atadza 5<unk>2 kuCao Yupeng mu16 yekupedzisira. Woollaston akakundwa muchikamu chekutanga cheAustralia Goldfields Open
, International Championship uye German Masters. Akaona Vinnie Calabrese naAlfie Burden nekurasikirwa kwechimiro chimwe chete kuti asvike kumakumi matatu nemaviri ekupedzisira eWelsh Open, kwaakasvika padhuze nekurova Ding Junhui asi akarasikirwa ne4 <unk> 3. Mumutambo mudiki weEuropean Tour mutambo weRuhr Open, Woollaston akakunda mukwikwidzi wepasi rose Ronnie O'Sullivan 4<unk>3 ndokubva achenesa Burden naChris Norbury 4<unk>0, vasati varasikirwa mune yekupedzisira furemu sarudzo kuna Stephen Maguire mumakota-fainari. Akaenderera mberi paAntwerp Open nekurova Joel Walker mumakota, asi O'Sullivan panguva ino akawana zviri nani zveWoollaston kuti akunde 4 × 2 mumasemifaira. Mhedzisiro iyi yakamubatsira kuti ave wechi20 paOrder of Merit kuti akwanise kuenda kuFinal kwegore rechitatu rakateedzana. Woollaston akarova Ding, mukundi wenguva ina parwendo rwemwaka uno, 4<unk>3 ave 3<unk>0 kumashure kuti afambire mberi kune 16 yekupedzisira yechiitiko chepamusoro kechipiri mumushandirapamwe uyu, kwaakabviswa 4<unk>2 naJohn Higgins.