5) Tottenham Hotspur – 363 Defeats
Spurs’s presence in the top five is mainly down to their years under the ownership of Alan Sugar. Their worst finish was 15th in 1994, when they lost 19 times.
In fact, they also lost 19 times during the 2003/04 campaign, and they have only lost fewer than 11 in a single season on ten occasions over the past thirty years.