Tottenham's 5 Biggest Regrets over the Past 12 Months

In the last 12 months, Tottenham Hotspur have changed manager, signed and sold a host of players and been involved in some high-stakes matches. 

It has been far from a disastrous year for Spurs, but there are always going to be regrets. 

No football club gets through an entire year without regrets unless they achieve a Barcelona 2009-10 sort of dominance. 

Let's count down Tottenham's five biggest regrets since March 2014. 

Defeat to Benfica in the Europa League

Francisco Seco/Associated Press

Last season's Europa League did not come with the added bonus of a Champions League place, but the competition (and its spiritual predecessor the UEFA Cup) holds a special place for Tottenham. 

Spurs won the Europa League in its first season and are always keen to bring its trophy back to White Hart Lane. 

In March 2014, Spurs' Premier League fate was largely sealed. Unlikely to drop out of the European places and with even less chance to threaten Arsenal's hold on fourth place, Spurs could have focused entirely on their European campaign. Spurs also have a proud record at home in European competition.  

In their first leg against Benfica, played at White Hart Lane, Spurs seemingly threw away any chance of progressing to the quarter-finals. 

A tie that could have been a genuine highlight in an otherwise entirely forgettable season was apparently lost after the first 90 minutes. 

The second leg was played in Portugal, but Spurs were the better side and remarkably fought their way back into the tie.

Two goals in two second-half minutes sparked Tottenham's European campaign back into life, but they couldn't find the vital third that would have forced extra time.   

Not Hiring Louis Van Gaal

Scott Heppell/Associated Press

Tim Sherwood was always at long odds to take the permanent job as Spurs' manager after stepping into the breach when Andre Villas-Boas was sacked in December 2013. 

Villas-Boas managed to talk himself out of the job with a series of poorly timed and poorly phrased "hard truths," and so Spurs were on the hunt for a new man. 

While Mauricio Pochettino was one of the men linked to the vacant position, most media coverage and fan interest was focused on the Holland manager Louis van Gaal. 

Van Gaal has a remarkable record with some of Europe's biggest clubs and a habitual trust in young talent. 

He seemed the perfect choice, but Manchester United's interest lifted him out of Spurs' range. 

When Van Gaal turned his attention from north London to Manchester, Spurs were left holding the bouquet. 

Instead of the Dutchman with the glittering resume, Spurs went with the lesser-known Southampton boss. 

The more Spurs fans learned about Pochettino, the less disappointed they likely became and, after almost a full season, virtually none would now count it as a regret.

Failing to Sign Mateo Musacchio

Alberto Saiz/Associated Press

Tottenham's summer 2014 priority was the rejuvenation of a defence that often reached absurd levels of incompetence in the preceding season. 

Michael Dawson was finally moved on, and players like Eric Dier, DeAndre Yedlin and Ben Davies were signed to add depth and potential. 

Spurs needed to bring in an experienced central defender who could potentially partner Jan Vertonghen and compete with Younes Kaboul. 

While they pushed hard for Mateo Musacchio, Spurs were unable to complete the deal with Villarreal. 

Instead, the club signed Sevilla's Federico Fazio, a giant of a man and a fierce competitor but a defender with some of the same flaws of the disposed Dawson. 

Fazio took some time to adapt to life in England, but he has proven a solid signing. 

Musacchio has enjoyed a solid season, either side of an injury that cost him several months, and reinforced the belief that he would have been a far superior option for Spurs to bring in. 

It is possible that Spurs will return to El Madrigal in the summer with a renewed bid, but they have missed a player with his combination of attributes. 

Emmanuel Adebayor

Tim Ireland/Associated Press

Emmanuel Adebayor may be the greatest enigma in Premier League history. 

Still one of the finest strikers in the division, when he is inclined to be, Adebayor has scored just once this season. 

Plagued by injury and remarkably varied personal issues, Adebayor is not the villain he is sometimes made out to be, but he certainly seems to be more trouble than he is worth. 

Mauricio Pochettino, as three Spurs managers before him, tried to find a place for the Togolese forward but has now seemingly decided to leave him out of the squad entirely. 

Adebayor has repeatedly proven himself a valuable player and an unnecessary distraction. 

The great regret of Adebayor is that there is a brilliant player there somewhere. He has scored many goals for Spurs and quite a few against them. 

Someone somewhere is presumably capable of coaxing that brilliance out on a dependable basis but, for all the progress he has made at Spurs, even Pochettino isn't that man. 

The League Cup Final

Tim Ireland/Associated Press

Tottenham's biggest regret of the last 12 months has to be the League Cup Final loss to Chelsea in February.

Any Wembley defeat is painful, but going down to a bitter rival after an inhibited performance made this one particularly tough. 

Chelsea did an excellent job of containing the same players that, just a month earlier, tore them apart in Spurs' 5-3 win at White Hart Lane. 

Tottenham fans are desperate to end their trophy drought, and this was a better chance than most. Having so recently beaten the Blues, Spurs knew they had a great chance, but it wasn't to be. 

Their young team will be back, and that defeat may be just the thing to make them mentally stronger for the bigger battles ahead, but it will remain the biggest regret of the last year.