Willie Waddell was Killie manager between 1957 & 1965 and guided the club to their only league win, lifting the famous old trophy in 1965.
Rangers winger Willie Waddell was Scottish football's biggest star in the immediate post-war era, and his foray into management did not disappoint either. 'The Deedle' took over in 1957 and would lead Kilmarnock through what was unquestionably a golden era. Killie hadn't been in bad shape – under Malky McDonald they had finished the 1956-57 season in third place – but Waddell took them to further heights, finishing as runners-up four times in five seasons between 1959-60 and 1963–64.
The 1964-65 season would be Killie's annus mirabilis, with the greatest result in their history coming early in the campaign. The club had been granted entry to Europe for the first time, and in the first round of the Fairs Cup they drew Eintracht Frankfurt. The Germans were famous in Scotland due to their European Cup exploits five years previously: they had contested that famous 1960 Hampden final with Real Madrid, having previously beaten Rangers 10-4 on aggregate in the semis. Erwin Stein, who scored twice against Real in 1960, would open the scoring in the first leg in Germany, Eintracht eventually winning 3-0.
The return leg at Rugby Park looked like a total waste of everyone's time, especially after Wilhelm Huberts lashed in a long-range shot after two minutes. But two quick goals, the first from Ronnie Hamilton, the other from Brian McIlroy, gave Killie hope. After resisting Eintracht pressure for the remainder of the half, the home side came again at the start of the second, James McFadzean heading home to make it 3-1 on the night, 3-4 on aggregate. Killie still needed two, and they left it late, John McInally levelling the tie with eight minutes to go before Hamilton, who had started it all off, notched the winner in injury time.