Crawford scored 43 goals in 66 matches in his first two seasons at the club. But arguebly the two seasons that followed were the most impressive of his time at Portman Road and must go down as two of the greatest in club history.
In 1960/61, Crawford scored an amazing 40 goals in 42 league matches, securing the Division Two title for Town. There was more to come however. In 1961/62 Town amazingly won the First Division, having only been promoted the season before, much of which was down to the partnership of Crawford (33) and fellow striker Ted Phillips (28) who scored an amazing 61 goals between them.
1962/63 saw Town's first foray into Europe, and was another successfull season for Crawford, who scored 40 times in 55 goals in all competitions. Changes were happening at the club though as in April manager Sir Alf Ramsey left to become the new manager of England in with just 6 games of the 63/64 season gone Crawford was sold to Wolves and Town finished the season bottom, and relegated back to Division Two.
Crawford stayed just 15 months at Wolves, scoring 39 times in 57 games before moving to local rivals West Brom. where he stayed little over a year scoring 7 times in 15 games before returning to Portman Road in March 1966 under then boss Bill McGarry, Crawford would score 8 times in the remaining 12 games of the campaign.
In the last three seasons of his Town career before leaving for Charlton in 1969, Crawford scored 53 times in 111 games. Whilst not as prolific as in his first spell at Portman Road, Crawford continued to be a major asset to Town and finished his second spell at Portman Road as a true legend to the fans lucky enough to see the striker play for Town over the years and to this day is still regarded as Town's greatest ever goalscorer.
Following his move to Charlton, Crawford represented both Kettering Town and Colcheser United before calling time on a hugely successfull career of a player who many feel was never given a chance to shine at full International level, where he earnt just two caps, both under Walter Winterbottom during the 1961/62 season, scoring his first and only international goal in a friendly against Austria at Wembley.