In his first two races at Hurst and Newbury, he unseated both Dick Francis and D. Dartnall before he was reunited with Captain Smalley, who knew how to ride the horse effectively.
With that in mind, Winter left Halloween to make his own running, and the pair won the Hurst Park Grand National Trial by eight lengths.
Showing marked improvement, Halloween started his campaign by defeating the top-class chaser Galloway Braes by ten lengths in the Grand Sefton Trial at Hurst Park.
Halloween prepped for the Cheltenham Gold Cup in the Herne the Hunter Handicap Chase at Windsor, where he conceded 2 stone 2 lbs in weight to Air Wedding and beat him by three quarters of a length.
Deprived of the rider who knew him best, Halloween won only his debut, beating former Cheltenham Gold Cup winner Cottage Rake (then a 14-year-old) over two miles at Wincanton.
Rated the second favourite, Halloween finished second to the outsider Gay Donald, who built up a commanding lead from the start to win by ten lengths.
[7] His final run of the season came in the Queen Elizabeth Chase, where both he and rival Galloway Braes ran below form behind Limb Of Law.
[9] Halloween ran only twice more, finishing second in the Bury Steeplechase at Fontwell and third behind 1953 Grand National winner Early Mist in the Brocas Chase at Windsor.
His longterm rival Galloway Braes was killed when falling in that year’s King George,[10] and Gold Cup winner Limber Hill broke down and never ran again.