It's fair to say that the Premier League era has been fairly underwhelming for Tottenham Hotspur. For such a huge club, they have underachieved enormously - managing two fourth placed finishes in the twenty-two years that the Premier League has existed (one of which didn't even result in a place in the Champions League). Two League Cups (in 1999 and 2008) are all Spurs have to show, in terms of silverware, in that time and it really isn't good enough. There have, of course, been some highs - the aforementioned cup wins, qualifying for the Champions League, an impressive performance in said Champions League and a 9-1 victory over Wigan Athletic which made Spurs only the second team to bag nine goals in a Premier League match - but it's fair to say that it has mostly been disappointing. The Premier League itself has produced some highly disappointing results for Spurs. They've taken some absolute thrashings, lost in matches in which losing meant missing out on something important and suffered agonising defeats to arch-rivals - and it's those matches we're going to be taking a look at here. Here are the ten most heartbreaking Premier League defeats for Spurs...
