Bunny Grant won the first event in the new National Stadium in 1962. Joy Foster made the Guinness Book of Records as the youngest ever senior national sporting representative at age eight (8) from any country, as also the younger of the only pair of siblings to win the award.
Sixteen year old Kingston Technical High School student, finished fourth in the 200 metres at the 1964 Olympics, Tokyo. Una also became the first repeat winner of either gender.
In later years, paraplegic competitors became only eligible for special awards.
Monica DeSouza became the first three-time winner and makes Table Tennis the most successful sport of the 60's with three female and one male win.
Foster, oldest brother of the first female winner Joy Foster, completed a record that has not been matched again in over thirty years, as they remain the only siblings to win the awards and the only ones also on different sides of the gender barrier.
The last year of the Machado Awards as the company is sold to the Carreras Group who wisely but not surprisingly considering their own leading role in sports promotion, decided to continue the awards. McCallum wins for his middleweight gold medal at the 1978 Commonwealth Games at Edmonton, only the second such outside of athletics at a major games. Hodges, probably Jamaica's fastest ever female starter and one of our best lead-off relay ladies ever, copped two silver medals in the 100 metres and relay, at the CAC games in Medellin, Colombia, that same year.
Weller wins two years in succession including the first year of the Carreras Award. In 1980 he became and still remains the only one of the forty-four Jamaican Olympic medallists to win one outside the sport of Track and Field Athletics. Merlene Ottey wins the first of a record thirteen awards, easily the most of sportsmen or sportswomen of either gender.
Cameron wins the 400 metres at the inaugural World Championship in the (Jamaican) city of Helsinki, Finland to continue Jamaica's remarkable record of winning the men's 400 metres Gold Medal at every single Games or Championships possible.
dominated the rest of the 1980's as he won World Titles at 3 different weights, at that time one of only fourteen men to do so from any country.
the fist hurdler to win the award and Juliet Cuthbert broke the Ottey monopoly as they won 3 silver medals between them at the Barcelona Olympics.
- became the first field event man to win the award based on his Silver Medal in the long jump at the 1996 Olympics in Atlanta, USA, while Deon Hemmings pioneereed splendidly as the first female Olympic Gold Medallist of the English speaking Caribbean, surpassing all the men also with Olympic records in both the semi-final and finals.
- Deon Burton becomes the first and only footballer to win the award and the only non-Jamaican-born Sportsman or Sportswoman ever to have won. Rene Simoes, Coach, and Horace Burrell, then President of the Jamaica Football Federation, both received the Chairman's Award.
completed a hat-trick of wins, and he became the oldest winner as he completed World Records of 519 Test Wickets, and the first man to get over 500 wickets in Test Cricket. On the ladies' side, Deon Hemmings and Lorraine Graham (now Fenton) created history by sharing the award, having both won two Silver Medals at the Sydney Olympics.
won as only the fourth man to set a 100 metres World Record among athletes not born in the United States, and the first such man to set this record not living in either North America or Europe. Trecia Smith, on the ladies' side created history as the first Jamaican Athlete of either gender to win a Gold Medal in a field event at the World level, having won the triple jump at the World Championship in Helsinki.