Cowdrey is remembered for two victories in particular. The first was against the West Indies at Port of Spain in 1967–68 when Gary Sobers made a surprise declaration and set England 215 runs to win in 165 minutes. Although he needed Ken Barrington and other players to overcome their natural inclination to safety (England had collapsed to 68/8 in the Second Test) he went out and hit 71 runs in 75 minutes for a 7 wicket victory with three minutes left. It was the last time England beat the West Indies in a series for 32 years. The second was in 1968 when Australia were 85/5 needing 352 to win when a deluge flooded the Oval and the players started packing their bags. Cowdrey called on the crowd to help the staff dry the ground and "like a modern-day King Canute he rolled up his trousers, waded into the water...and supervised the mopping up operations of hundreds of volunteers". Derek Underwood took 7/50 and England won with 226 runs and six minutes to spare.