Dempsey, who made the move to White Hart Lane from the cozy comfort of Fulham's Craven Cottage in August, has experienced some growing pains in North London, but he has been able to contribute in critical positions this season.
The obvious highlight of Dempsey's season came during his two against Manchester United on September 29 and January 20.
Dempsey scored the third and eventual game-winning goal at Old Trafford in September before he netted a 90th-minute equalizer at White Hart Lane four months later.
While the American did make an impact on the North London club with his flare for the dramatic, his role in the first team has not been guaranteed all season.
Injuries have played a part in keeping Dempsey out of the starting 11, and so has the emergence of Gareth Bale in the center of the midfield attacking trio, a position that Dempsey fits in the best at.
Now with Bale on the bench because of an ankle injury, Dempsey has been thrust back into the lineup and has given Tottenham plenty of quality minutes on the pitch.
Overall, Dempsey has played in 33 matches in all competitions, 23 of them being starts, and he has scored seven goals while providing five assists.
The offensive output of Dempsey would be considered good by any American fan had the 30-year-old not racked up a 23-goal season at Fulham just a year ago.
With American fans focused on the numbers, the expectations of Dempsey will always be for him to his career-high goal tally from the 2011-12 season.
As we look ahead to next season, fans of the United States and Tottenham must not expect the man affectionately known as Deuce to light the back of the net on fire.
However, it is right to expect Dempsey to be in the starting 11 on a consistent basis. Dempsey does fit well in the 4-2-3-1 system that Spurs manager Andre Villas-Boas employs on a weekly basis by playing in the center of the attacking midfield trio.
By being put in the center of the midfield, Dempsey has freedom to roam throughout the pitch and create chances. But he needs to learn to play effectively on the wing as well.
The biggest question surrounding Tottenham's summer moves will be if Gareth Bale moves away from the club in a big-money transfer or stays in North London for another season. The potential departure of Bale would benefit Dempsey because he would be the clear first-choice player in the central midfield as well as being cast into the role of superstar.
Dempsey thrived in the role of club superstar for his final two seasons at Fulham, and he would not have a problem going right back into the spotlight next season.
If Bale does not move, which is a big if at the moment, Dempsey will most likely be asked to compete for the third role in the midfield alongside Bale and Aaron Lennon. Time and time again, Dempsey has proven what a versatile player he is, and there is no doubt in his mind that he could beat out Gylfi Sigurdsson and Lewis Holtby for a starting spot.
Regardless of what happens around him at Tottenham this summer, Dempsey will once again have to maintain his high level of fitness and hope to avoid a freak injury during CONCACAF World Cup qualifiers with the United States.
If everything falls in Dempsey's favor, it is close to a guarantee that he will be making a big-time difference for Tottenham next season at the club and continental levels because of his versatility.
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