Whakakiia te rerenga e whai ake nei: He maha nga hōtaka a Winkleman i te waa nui. I te tau 2007, i riro ia i a Cat Deeley hei kaihautu matua mo te raupapa tuatoru o "Comic Relief Does Fame Academy", e mahi tahi ana me Patrick Kielty. I whakahaeretia e ia te whakataetae kanikani Eurovision 2007 i te taha o Graham Norton mo BBC One i te marama o Hepetema o taua tau, a i te tau i muri mai.
Ko te tau 2008. I whakaatuhia e ia te tukanga whiriwhiri a UK mo te Eurovision Song Contest 2008 i huaina ko "", i tenei wa e haere tahi ana me te Eurovision stalwart Terry Wogan. I te Poutu-te-rangi 2008, i whakahoutia e Winkleman tana hononga ki a Kielty i te wa i whakahaerehia e te tokorua te waahanga whakamutunga o te "Sport Relief 2008".