1959 NSW Federation Cup

The 1959 NSW Federation Cup was the third edition of the NSW Soccer Federation's premier soccer cup. This was the first time the tournament received sponsorship by W.D. & H.O. Wills and called the "Ascot Thousand" after their popular cigarette. The cup was contested by all fourteen first division clubs and the top two placed second division clubs in the premiership. The £1000 prize money was divided among the first four placings, with first place receiving £600, second place £250, third place £100 and fourth place £50.

Canterbury-Marrickville were the defending champions, having beaten Sydney Prague 3–2 in last year's final. They were eliminated in the semi-finals but won the third place playoff match, defeating Budapest 5–2.

The final was played on 25 October 1959 between Sydney Prague and Sydney Hakoah. Hakoah won the match 2–0 to claim their first title.