 Nyorai kuenderera mberi kweiyi ndima - Mushure mekurova chinangwa pamitambo miviri yeDarlington, Gregg akabatana neSheffield Chitatu pamberi pemwaka wa1928 29, uye akavabatsira kuhwina mukwikwidzi weFirst Division wegore iro. Mumwaka unotevera, akarasikirwa nenzvimbo yake kuna Harry Burgess, uye muna Ndira 1931 akabatana neBirmingham nemubhadharo we 2,200. Akatamba chikamu chake mumushandirapamwe weFA Cup mwaka iwoyo, uye akarova chinangwa mu1931 FA Cup Finalrakanga risingabvumirwi nokuda kwokusava nomutambo. Akatamira kuChelsea munaGunyana 1933 nemari ye 1,500, achipedzisa basa rake neBoston United muMidland League uye neSligo Rovers muIreland munguva yeHondo Yenyika Yechipiri. 