Tottenham won London derbies against West Ham United and Arsenal, established a decent lead heading into the San Siro for their return leg meeting with Internazionale and then capitulated in embarrassing fashion at Liverpool.
All of this will of course mean something to the injured Dempsey, but there have also been developments that will have been of interest to him individually.
A move to a more central position for Gareth Bale was already being mooted. That has come to fruition now, but also in the American's absence, Gylfi Sigurdsson has staked a serious claim for Spurs' remaining midfield place.
The arrival of Lewis Holtby and his own failure to make the most of starting opportunities (a disappointing FA Cup appearance against Leeds United stood out) had seen Sigurdsson marginalized. This writer was one who suggested that it would be primarily be a battle between Dempsey and Holtby for the attacking midfield positions not occupied by Bale and Aaron Lennon.
Sigurdsson has demonstrated how quickly things can change in football. A vital equalizer against West Ham was followed by positive performances against Arsenal and Inter Milan, reiterating his value to Andre Villas-Boas. Helpful timing, giving the manager another option in his attempts to finish his first season with Spurs successfully.
For Dempsey, Sigurdsson's emergence and Bale's re-positioning means he has real competition at hand when he recovers from his calf injury (he is scheduled to return sometime in the next couple of weeks). Even prior to his injury and these changes in circumstances, Dempsey had been experiencing a lull in which what was next for him was not clear.
A good couple of month's worth of performances had given way to some less effective showings. The effort was evident, but there were issues relating to a lack of goals with Tottenham (at one point or another) without the services of Jermain Defoe and Emmanuel Adebayor. Even with the strikers around, they were experiencing dry spells too.
Dempsey has not yet had a chance to show how he might coexist in a lineup that now features Bale in his previous position in and around a lead forward.
Depending on the form of Defoe (and possibly Adebayor) in the coming weeks, Villas-Boas feasibly could consider using Bale up top—in which case Dempsey might see action sitting just off of the Welshman. More likely, though, he will be fighting it out with Sigurdsson and Holtby for a spot in left midfield.
Though back in contention, Sigurdsson has not done enough to claim that place as his own. The loss to Liverpool highlighted his inability to offer much penetration when Tottenham do not have as much possession up the field. In fairness, this lack of directness was exacerbated without Lennon's pace on the opposite flank.
Would things have been different with Dempsey or Holtby there instead? Neither has too much speed, but the energy of Holtby or Dempsey's nous in advanced positions may have changed things up slightly.
They have differing tempos and idiosyncrasies in how and where they like to receive the ball, as well as how they link up with teammates. Villas-Boas will soon have to decide if one of the three stands out, or if he will alternate depending on the opposition.
Dempsey may have to wait his turn for a game or two once he regains fitness, but even then he is likely to see some involvement off the bench. His manager will not automatically restore him to the side if others are playing well. Yet, Villas-Boas has come to appreciate the USA international's habit of popping up with an important goal or assist.
That is something the 30-year-old has proven already this season, and but for being injured, might have done so in recent weeks too. The upcoming test for Dempsey will be in his ability to adapt to a team that is evolving under Villas-Boas' management.