 Nyorai kuenderera mberi kweiyi ndima - OSullivan akatanga mwaka wa2008-09 nekukunda Northern Ireland Trophy, achikunda Dave Harold 9-3 mumutambo wekupedzisira. OSullivan ndiye chete mutambi akakunda zviitiko zvekuronga kumashure-kumashure mumakore mana apfuura. Akazosvika kumagumo eShanghai Masters, achinge akunda Stephen Maguire mumasemifinal aine maviri epamusoro kuputsa kwe141 ne145. Zvisinei, mumutambo wokupedzisira, akakundwa 810 neRicky Walden. MuPremier League, akawana 72 kukunda Mark Selby, izvo zvaireva kuti akahwina mutambo uyu kasere, uye kashanu akateedzana. Zvisinei, OSullivan akakundikana kudzivirira UK Championship yakezita, achirasikirwa naJoe Perry 59 mumutambo wechipiri. OSullivan akanga abvuma mutambo wegumi nembiri wemutambo kuti aende 57 pasi, kunyange zvazvo Perry akabata kutungamirira kwemapoinzi 23 chete ku zero. Achitaura pashure pacho, OSullivan akati Zvingadaro zvakaita sokuti ndakarasika pfungwa dzangu kana chimwe chinhu, asi ndine chokwadi chokuti ndichadzoka. Nokuda kwaikoku gare gare akabhadhariswa 300, uye akarayirwa kubhadhara 1,000 mumitengo. 