He was a prolific goalscorer who played for eight teams, scoring 256 goals in 535 League appearances and winning seven full international caps for Scotland.
MacDougall joined Liverpool as an apprentice in 1964 and, on the day he turned 19, he was offered a professional contract at Anfield by manager Bill Shankly.
However, MacDougall did not make it at Liverpool, where Ian St. John, Roger Hunt and Tony Hateley shared the goal-scoring duties, and made no first-team appearances.
Despite MacDougall's signing, and the 21 league goals he contributed, the Cherries were relegated to the 4th Division in 1970 and Freddie Cox was sacked by the then chairman Harold Walker.
That season also saw the club record for the number of goals scored in a game smashed as MacDougall put six past Oxford City in an FA Cup replay that eventually finished 8–1.
On 20 November 1971, MacDougall netted an extremely rare "triple hat-trick" in Bournemouth's 11–0 victory over Margate in the first round of the FA Cup.
[4] MacDougall scored five in the first half – at which point the Margate boss jokingly asked Bond to substitute their tormentor[citation needed] – and another four after the interval.
Aside from his Margate exploits, he also hit the headlines in February of that season for his spectacular flying header away to Aston Villa in front of a 48,000 crowd and the Match of the Day cameras.
[citation needed] Wolverhampton Wanderers, West Ham United, Coventry City and Crystal Palace were all chasing the striker over the summer of 1972.
[citation needed] MacDougall stayed and pledged his loyalty to Bournemouth, but in September 1972, John Bond accepted an offer of £200,000 from Manchester United.
He made a scoring debut against Sweden, and managed three goals in seven games before being passed over as competition for places in the Scottish team was fairly intense at this time.
At Southampton, he scored 23 league goals in his first season, playing alongside players such as Mick Channon and Peter Osgood, although they were unable to gain promotion to Division One.
Benson was soon replaced by Alec Stock and things were on the up after his first game, in which the Cherries thumped Doncaster 7–1, but the good fortune did not continue as Bournemouth finished in 18th place.
In February 1980, MacDougall left Bournemouth to join Alan Ball's Blackpool as player-coach until October 1980 and thereafter was restricted to occasional matches in non-League football at Salisbury City, Poole Town and Gosport Borough.
In July 2013, the redeveloped southern stand at Bournemouth's Dean Court stadium was named after MacDougall in recognition of his service at the club.