Bregawn ran seven times during this season, winning on five occasions, and culminating with victory in the Cheltenham Gold Cup. After beginning the season with victory in a minor event at Newton Abbott in October, Bregawn was not hard pressed to win the four runner Rehearsal Chase at
Chepstow in early November. Bregawn then lined up for the
Hennessy Gold Cup at
Newbury on the final Saturday of November. Ridden by his now regular rider Graham Bradley, Bregawn carried the second top weight of 11
stone 10
lb, 2 lb lower than the top weight,
Night Nurse. Starting the 9/4 favourite, he fought out the later stages of the race with his stable companion Captain John, to whom he was conceding 10 lb. In an exciting finish, Bregawn made a bad mistake at the final fence, nearly unseating Bradley, and started the run-in three lengths behind his rival. He then found extra reserves to chase down and pass Captain John and passed the line three lengths ahead. Describing the performance, Timeform stated," the closing stages of the Hennessy underlined Bregawn's battling qualities and his tremendous zest for racing." Bregawn was beaten in his next start, the
Tommy Whittle Chase at Haydock Park by his sole rival, the 1981 Cheltenham Gold Cup winner
Little Owl. Bregawn was said to have pulled a muscle and this would keep him out of the
King George VI Chase. Bregawn was next seen on 24 February in the
Jim Ford Challenge Cup at
Wincanton. In a seven runner event, he started the 6/5 favourite and was beaten half a length by Comb's Ditch. The Timeform representative at the course reported that Bregawn was "very much in need of the race - he looked quite distressed afterwards and blew very hard". A field of eleven lined up for the 1983 Cheltenham Gold Cup run on soft ground. Bregawn went off the 100/30 favourite ahead of Comb's Ditch at 9/2. Then came two of Bregawn's stable companions
Silver Buck and
Wayward Lad at 5/1 and 6/1 respectively. The
Fred Winter trained pair of Fifty Dollars More and Brown Chamberlin came next in the betting followed by the other two Dickinson runners, Captain John and Ashley House. In a race famous for Michael Dickinson training the first five home, Bregawn went to the front at the fifth fence and remained ahead from then on, seeing off the strong challenges of stable companions Captain John and Wayward Lad in the later stages of the race. Bregawn passed the post five lengths ahead of Captain John, with a further length and a half back to Wayward Lad in third. There was then a large gap back to the other two Dickinson runners, Silver Buck and Ashley House. Bregawn ended the season as Timeform's best staying chaser, with a rating of 177, behind only the two-mile champion
Badsworth Boy, another Michael Dickinson trained horse who received a rating of 179. Bregawn would never repeat the level of the form shown during this season. In respect of the Gold Cup performance, Graham Bradley is on record as saying, " I firmly believe that he was so brave that day and put in so much effort that he was totally exhausted. It blew his mind and, a bit like a boxer who wins a championship but gets badly beaten doing it, Bregawn just didn't want to go through the pain barrier again". == 1983/1984 season ==