1957—1959: Consecutive Brownlow Medallists
In 1957, Brian Gleeson became the second St Kilda player to win the league's highest individual award, the Brownlow Medal.
In 1958, Neil Roberts became the third St Kilda player to win the Brownlow Medal.
Also in 1958 St Kilda won the Consolation Night Series competition, a competition that was played between clubs that had failed to qualify for the premiership season finals series. St Kilda defeated Carlton 16.13 (109) to 15.11 (101) in the final.
In 1959, Verdun Howell became the fourth St Kilda player to win the Brownlow Medal.
Howell tied with Bob Skilton in the 1959 Brownlow Medal count. At the time Skilton was awarded the medal on count-back. The league later decided to award a Brownlow Medal to any player who was eligible to win who tied on the same number of votes as a winner who won on count-back – with Verdun Howell receiving a Brownlow retrospectively.
In 1961, after finishing sixth in 1960, Allan Jeans was appointed coach. St Kilda qualified for the final four for the first time since 1939, qualifying third with eleven wins and seven losses. However, with fullback Verdun Howell unfit, the club lost to Footscray in the first semi-final. The club finished ninth in 1962 with nine wins and nine losses.
In 1964, St Kilda were defeated in the final of the Consolation Night Series competition by Footscray 11.12 (78) to 11.7 (73).
St Kilda had a convincing sequence of six consecutive wins in the last six rounds of the 1963 season to qualify in fourth position with 13 wins (52 premiership points), two premiership points behind minor premiers Hawthorn. The club lost to Melbourne in the semi-finals.