As a four-year-old Highland Fling developed bad barrier manners spoiling his chances of winning races and he was transferred to the stables of Leo Berkett who reduced the amount of gear (equipment) that he was wearing.

On the same day as the second mile time trial, he won the Premier Sprint Championship.

[5] In April 1949 he beat Captain Sandy at Addington but a broken bone in a leg ended his career.

[7] In his career Highland Fling won 25 races with 6 second- and 4 third-placings from 70 starts and £32,920.

[7] Highland Fling was an inaugural inductee into the New Zealand Trotting Hall of Fame with the immortals Caduceus, Cardigan Bay, Harold Logan, Johnny Globe and Ordeal.