1884 – 1945
Sydney Middleton was a member of the First Wallabies who represented Australia in rugby union at London 1908. Australia won the gold medal in the two-team competition by defeating the then current English county champions, Cornwall, representing Great Britain, with a score-line of 32-3.
Middleton's next Olympic appearance was at Stockholm 1912 as a rower. The Australian eight-oared crew was primarily the one that had convincingly won the Grand Challenge Cup at the Henley Royal Regatta earlier in 1912. But for a change in the crew between Henley and Stockholm and then having to row in a less advantageous station in the semi-final at the Olympic regatta the Australians should have won an Olympic medal, perhaps the gold medal. The victorious crew at Stockholm was from Great Britain and was from the club convincingly beaten by the Australians at Henley.
Middleton was highly decorated in the Great War and after the warring parties agreed to stop fighting was integrally involved in arranging the sporting events for the allied troops prior to their returning to their homes. One event was the Royal Peace Regatta where the cup presented by King George V for eight-oared boats was won by an AIF (Australian Imperial Forces) crew. Middleton was also a member of the victorious crew. In time, that cup, the King's Cup, became the trophy presented to the winning eight at the annual Australian interstate rowing competition.