Spurs travel to Italy to take on Fiorentina in the Europa League before facing Chelsea on Sunday in the League Cup final at Wembley.
Both tournaments are vitally important, but playing his strongest XI in Florence could hinder the side’s chances of winning silverware against Premier League leaders Chelsea on Sunday.
It’s a tough decision for Pochettino, and speaking to reporters ahead of the match the Argentine admits he still doesn’t know what the best course of action will be,.
"I think this is our first final before Sunday as Fiorentina are only one game from going into the next round,” he was quoted as saying by the Daily Star.
"We know that we need to score with the score being 1-1 but we are confident. We are confident to take the game on Thursday and try to get the victory.
"We need to decide on who plays because we have played two very tough games against Fiorentina and West Ham. So we need to analyse and decide the strongest team to play."
Should Spurs play their best XI against Fiorentina?
While in an ideal world Spurs would have taken a healthy lead going in to their second leg in Florence, the reality is they need to go there in search for goals after drawing the first leg 1-1 in North London.
A Europa League triumph in May would guarantee a place in next year’s Champions League, but a League Cup final represents as big a chance as they may have for silverware this season.
In a bid for goals, the dynamic trio of Christian Eriksen, Mousa Dembele and Harry Kane have to start. However, a long Thursday night could cause potential burnout ahead of Sunday’s clash with the Blues.
Pochettino is in a tricky position, and resting players on Thursday – and losing – followed by a League Cup defeat would be a major blow and could prove detrimental to confidence in their bid to finish in the top four.
Whatever the Argentine’s decision – right or wrong - the Tottenham fans need to take into consideration the immense hard work which has gone into getting the team to such a position and back them to the hilt.