Scoring twice in a 4-2 friendly win over Germany, the United States national team captain then led his team to three consecutive World Cup qualifying wins. Jurgen Klinsmann's side currently top the CONCACAF group by two points with four matches left to play.
Dempsey is, without doubt, one of Klinsmann's main men. Less certain, heading into the new season, is his status at Tottenham.
The 30-year-old started 22 times in the Premier League last season, featuring in a further seven games as a substitute. In addition, he saw involvement in 14 of Spurs' cup fixtures, all adding up to 43 total appearances.
Considering Dempsey missed some games through injury, it was a solid return for his first season at Spurs. Performance wise, he picked up over the course of the campaign and became a valuable, if slightly unsung, contributor—both in goals and his general play.
Undeniably though, the American's role was a diminished one in comparison to that which he had come to occupy at his former club Fulham.
In order to join a team he deemed more capable of challenging for major honors and reaching the Champions League, it was a reality he had to be prepared to accept.
With that said, Dempsey was a regular start up until mid-December. As the season moved into winter, he was looking like he had settled into his duties and position—mostly playing just off a lone-striker—with it showing in the increasing quality of his performances.
With unfortunate mistiming, he missed the Christmas period through injury just as he was gathering some momentum. Thereafter the situation changed (notably, Gareth Bale really stepping up his game and Lewis Holtby joining), leaving Dempsey less guaranteed of a start.
That is a situation he is facing again as Tottenham return for preseason. The signing of Paulinho has increased the competition for places across the midfield—even should one or two potential rivals depart.
At this point we have little idea of manager Andre Villas-Boas' intentions for his team this season. This is true in regard to Dempsey as well.
Spurs went to some effort to sign him last year, so it would be surprising to see him deemed surplus to requirements. With the hunt for a top-class striker ongoing, Dempsey is just too valuable a source of goals (among other things).
Keeping up his goalscoring habit will be integral to the attacking midfielder's first-team chances.
His tally of 11 in 2012-13 was a decent enough return. Particularly pleasing for Villas-Boas was the importance of some of these goals—strikes that demonstrated Dempsey's big-game aptitude.
A winner and an equalizer in league games against Manchester United gave Spurs their best return off the Red Devils in a single campaign since 1995-96.
As the race for Champions League qualification heated up in spring, Dempsey scored big goals in vital wins over Manchester City and Stoke City. A brace against Basel temporarily kept Spurs' Europa League hopes alive in a tough quarterfinal second-leg out in Switzerland.
If Dempsey is not playing to begin with, it will be hard to repeat this. But even coming off the bench, he knows he has a knack of grabbing a goal—something that can help convince his coach of his merits.
As obvious as it to say, application is a must for Dempsey. He most show himself to be willing to do a job wherever Villas-Boas plays him.
Out wide this means doing a defensive shift while still involving himself as much as possible when his team has possession. In central positions, he must make the most of his nous and be a constant option for his teammates.
Being a utility player is not necessarily glamorous, but to play for a team with aspirations as lofty as Tottenham's, some men have to take what they can get.
How any of this might pertain to Villas-Boas' bigger plans remains to be seen. But while Dempsey remains a star for the United States, his potential success at Spurs likely involves embracing a future as a workhorse—albeit one still capable of moving into the limelight.