Juande Ramos is currently in charge of Ukrainian Premier League outfit Dnipro and Spurs will face their former boss in the opening leg of their round-of-32 Europa League tie at the Dnipro Arena on Thursday evening.
UEFA still expect the game to go ahead despite plans for a day of mourning in Ukraine following the political unrest in Kiev.
Dnipro are based in the city of Dnipropetrovsk, 220 miles away from Kiev, where scenes of death and bloodshed continue to be beamed around the world as police clash with government protestors.
Ukraine's president, Viktor Yanukovych, has declared February 20 a day of mourning for the victims of the clashes but UEFA insists Thursday's match will be unaffected.
Dawson is expected to lead a much-changed Spurs side into the opening leg, admitting taking the club's first piece of silverware since Ramos delivered the League Cup in 2008 would be a proud moment.
"It is a great chance," he said.
"It is our last chance and it is a competition we took seriously in the group stages - come the end of the season I could be lifting this trophy and that would be a massive honour.
"We have been in the Champions League in the time he [Ramos] has moved on.
"I had a hard time under Juande Ramos, there was no hiding it, but he brought silverware to the football club
"We would like to have won more silverware since then. We are striving high, we know are aims, we want to be in the Champions League spots."
Dawson went on to suggest his unhappy period under the Spaniard, who lasted just under a year at White Hart Lane, was down to his own form and that it was not simply Ramos taking a dislike to him.
"What went on when Juande was manager is history to me," he said. "I wasn't in the team, we had top players in the club at the time.
"I have nothing against him, it was a difficult time for me as I wasn't performing as well as I know I can and I have to take responsibility for that - the manager is there to pick the team."
Dawson remains keen for the Tottenham squad to focus solely on their football whilst in Ukraine and not get sidetracked by the events in Kiev.
"We have come over here to play football," he added.
"It is not for us to comment what is happening in Ukraine. We are here to concentrate on football. Ukraine is a tough place to come but it is about us."
Head coach Tim Sherwood echoed his skippers' comments about keeping the club's intentions based purely on the field in Dnipropetrovsk.
"No security travelled on the plane or at the hotel, we feel comfortable," he said.
"We just concentrate on the game. It is never great to see violence in any country at any time but it is something we are not concentrating on. We will do our job. Hopefully when we leave tomorrow we will be happy."