The first tournament was in 1929. Late in the day, the clubhouse leaders entered a playoff to determine the championship. Unbeknownst to them, Maurice Kearney was still on the course with a chance to win. While he was on the 18th hole, he notified the players in the playoff, who were playing on the first hole, that he had a chance to win outright. Kearney did indeed win outright and "the playoff" was terminated. The following year George Siebert won the event defeating Peter Manning, who was also runner-up the previous year, in a playoff. In the early 1930s, the tournament was dominated by
Gene Kunes and
Joe Turnesa. Kunes won the tournament in 1931 and 1933. The following year, as defending champion, he was considered to be the favorite. However, it was Willie Hunter who took the lead after the first three rounds. He led by four over Turnesa entering the final round. However, in the final round Turnesa birdied the first two holes and the tournament suddenly "cracked wide open" when Hunter triple-bogeyed the par-5 5th hole. Hunter continued to struggle and Turnesa expanded his lead. Despite bogeys on the final four holes Turnesa won easily. It was later decided that the tournament would be moved up a couple months earlier, in August. In April 1936, the Connecticut Section PGA made a number of changes. The "most important decision," according to
The Hartford Courant, was to extend the Connecticut PGA Championship to 72 holes. The following year, in 1937, the tournament took a "radical departure" and changed its format to match play. In May 1941, however, the Connecticut PGA decided to return to a medal play format. In the late 1940s, the tournament was dominated by Eddie Burke and Harry Nettelbladt. Burke won the tournament in 1945 and 1946. The following year, Burke led the qualifiers while Nettelbladt finished second. Both players made it to the finals. In the morning round of the finals, Burke "coasted" with a 71 (−2) to take a 5 up lead. During the afternoon round, however, Nettelbladt produced a "sensational performance," ultimately scoring a 65 (−8) and tying the match. After halving the first extra hole, however, Nettelbladt took four shots to reach the green of the par-4 38th hole. He made bogey to lose to Burke. Two years later, in the finals, Burke "set an all time record" defeating Frank Staszowski 12 & 11. In the 1950s, the tournament was dominated by Bob Kay, a professional at
Wampanoag Country Club. In 1953, he made it to the finals. Kay took a 5 up lead in the morning round however Burke tied him during the afternoon's back nine. Kay, however, won the 15th and 16th holes to secure the match and championship. He won 2 & 1. Kay won the tournament again in 1956 and 1959. It was the second time they met in the finals, the first in seven years. Both were intending to win their fourth title. Kay "got off to a strong start" and took a 6 up lead after only 8 holes. Over the course of the rest of the match, however, Burke "slowly but surely whittled Kay's lead down." Entering the final hole of regulation, he was only 1 down. However, Burke failed to make the green in regulation and conceded the hole. Kay won 1 up. In the early 1960s, there were some changes. In 1961, the tournament returned to medal play. The following year the tournament returned to Connecticut after having been held in Massachusetts the previous year. ==Winners==