The son of former jockey Jimmy Dearie, Tom Dearie rode 31 winners over jumps in the 1950s. He served his apprenticeship with Charles Elsey at Malton from 1940 to 1946 and then spent a year with Bill Dutton. He rode ten winners as an apprentice and then rode as a freelance on the Flat between 1948 and 1952 but found rides difficult to come by. He rode just one winner during that time, on the John Bowness-trained two-year-old filly Bit of Fluff at Carlisle on July 5, 1951.
In 1953 he took out a National Hunt jockey’s licence and relocated south to join Wimborne, Dorset, trainer Peter Payne-Gallwey, for whom he would ride most of his early jumping winners. He had his first winner over jumps on Earlswood at Warwick on December 12, 1953. He rode four winners during the 1954/55 campaign, including two over the Easter period at Wincanton and Chepstow,
Having taken over from Ted Fisher as Peter Payne-Gallwey’s stable jockey, he doubled his score to eight the following season, thanks largely to a chestnut mare named Signorita. They made a bright start, winning novice chases on successive days at Newton Abbot in August, following up at Newton Abbot and at Taunton in September, then graduating to handicap company and winning twice more, at Hurst Park in October (left) and Ludlow in November. That Ludlow victory completed a first/last race double for Tom, having won the opener on Payne-Gallwey’s novice hurdler Ugogo.
Signorita was one of Tom’s six winners the next season. He went to live in Canada in 1957 but came back a year later. He booted home five winners during the 1958/59 campaign, including a double at Worcester on March 2, 1959, landing both divisions of the Hallow Novices' Hurdle on Dalstar for Major Edward Champneys and Prince Conkers for Ted Fisher.
Five more winners followed in the 1959/60 campaign, the last being on the Ricky Vallance-trained Aryaman in the Leominster Handicap Hurdle at Hereford on Whit Monday, June 6, 1960, in which he beat Terry Biddlecombe on the favourite Mustang’s Glory by a short-head. That proved to be the final winner of Tom’s career but beating a Biddlecombe-ridden favourite by the narrowest of margins wasn’t a bad way to finish.
After retiring from the saddle he became the popular landlord of the Malt Shovel pub in Lambourn.