Having made his desire to leave the Cottagers clear, Dempsey had been spending a lot of time doing solo sessions over the past few weeks.
The situation was brought to an end on Friday when the 29-year-old completed a move to Tottenham and he joined up with his US colleagues soon after ahead of the team's CONCACAF World Cup qualifying Group A double-header against Jamaica.
The first of those games is in Kingston tomorrow and speaking about his preparation for the clash, Dempsey told www.ussoccer.com: "It was good. It was good to get back into the team, with the guys, and good for me to get back into training.
"I've been training with a trainer, but it's good for me to get back in playing with team-mates."
Following Friday's contest, the USA and Jamaica - who are currently joint-top of the group on four points from two matches each, with the former having a superior goal difference - meet again on Tuesday in Ohio.
Contemplating those two games together, Dempsey said: "You could look at it as a play-off fixture in the sense that there is a home and an away leg.
"We just need to make sure we get the points because they're vital and we need to make sure we put ourselves in the driver's seat so that we qualify for the next round.
"Everybody wants to be part of a World Cup and for some of these guys it'll be their last chance to do that.
"I think everybody here wants to do something special and playing in a World Cup is certainly that."
Friday's other game in Group A sees Guatemala host Antigua & Barbuda, while in Group B, there is another top-two clash as first-placed Mexico travel to Costa Rica.
The group leaders have six points from two fixtures so far but are travelling to a place where Spain and Argentina were both held to draws last year, and Mexico coach Jose Manuel de la Torre is certainly not about to take Costa Rica lightly.
"We have seen the circumstances in which Costa Rica have lived with their rivals," De La Torre told reporters.
"We are very respectful of our opponents and we know that no place is easy."
Elsewhere in Group B, El Salvador face Guyana at home, while Group C's games see second-placed Canada take on leaders Panama in Toronto and Cuba and Honduras go head-to-head in Havana.
After six rounds in this phase, the top two teams from each group go through to the final stage, to be played next year.
The top three sides then qualify directly for the 2014 World Cup in Brazil, with the fourth-placed team facing a home-and-away play-off against a team from Oceania.