In the League Cup of 1969, Celtic had successfully negotiated a section involving Rangers, Airdrie and Raith Rovers, with Willie Wallace getting 4 goals and both Harry Hood and John Hughes notching 3 in the six-match total of 21.
After a goal-less first leg in the quarter-final against Aberdeen at Pittodrie, counters by Wallace and Bobby Lennox in the return at Parkhead gave Celtic a 2-1 win to put them into the semi-final, against Ayr at Hampden – where the Honest Men sprang a surprise, the match going to extra-time.
In spite of three Celtic goals, through ‘Big Yogi’ Hughes, Tommy Gemmell from the penalty spot and Bertie Auld right on time, Ayr also scored three to take the tie to a replay, which was held on this day in 1969, again at Hampden. Nearly 48,000 turned up – 15,000 more than for the first match – and saw Ayr open the scoring in the 12th minute but Celtic equalised two minutes later through Harry Hood and got the winner through Steve Chalmers in the 54th minute.
!2 minutes from the end, Ronnie Simpson dislocated his shoulder again, an injury which effectively finished his wonderful career.