10 Most Expensive Man Utd Transfer Flops In History

2. Ted MacDougall (£200,000)

Despite starting his playing career at Liverpool, it was at Bournemouth where Ted MacDougall came to prominence, earning a reputation as a prolific goalscorer in the fourth and then third divisions of English football. MacDougall had a Lionel Messi-esque goalscoring record for The Cherries, plundering 103 goals in 146 appearances - form which unsurprisingly led to United making their move for the forward in 1972. A then-massive £200,000 was splashed out - £29 million today - and MacDougall was expected to step into the shoes of Denis Law and Bobby Charlton. That never happened. The former Liverpool man scored a depressing five goals in 18 total appearances for the Red Devils, and when Tommy Doherty replaced Frank O'Farrell as manager in 1971, the new man in charge deemed MacDougall surplus to requirements after just a year at the club, selling him to West Ham United.