Bill McGarry saw his Ipswich side plummet down the league table during the 1965 – 66 season as they could only manage to finish the season off in a disappointing 15th place finish in the second division with their results slowly deteriorating as the campaign progressed. The following year saw a resounding improvement in the clubs league fortunes as they finished the campaign off in an impressive fifth place also managing to reach the fifth round of the FA cup, suffering defeat against Manchester city in the last sixteen. The 1967 – 68 league campaign proved to be their last season playing second division football as they finished the campaign off as champions of the second division in turn promotion the club to the top flight. Mick Mill began to establish himself as a fine left back at Portman Road. Bobby Robson was installed as the new Ipswich town manager in the year 1968 and his first full season in charge at the club saw Ipswich finish of in a very decent 12th position in the top flight.
The 1969 – 70 campaign saw Town involved in a relegation battle as they finished off the term in 18th place; however they secured their first division status with few weeks to spare.
Ipswich were eliminated out of both the FA cup and league cup in the third round of the competition, suffering defeats against West Brom and Manchester United respectively.