Glen Hoddle continued to criticise Tottenham's FA Cup performance after his former side was knocked out of the tournament on Wednesday.
Spurs have not won a trophy for over 15 years and seemed to have an excellent chance to progress as they faced Championship side Sheffield United in the quarter finals.
Things did not go to plan, though, as a weakened side that did not include the likes of Harry Kane and Dejan Kulusevski were beaten 1-0.
Hoddle was less than impressed with the performance, and when asked on BT sport if Wednesday's Champions League tie with AC Milan was Spurs' most important game of the season, he replied: 'the quarter finals of the FA Cup might have been their biggest game if they had played the right team, but now this is their biggest game.'
It continued a complaint he had made the night before, when he told the same broadcaster the midweek loss was: 'a crushing blow because it's the only realistic trophy they could've won.
'I don't know why they didn't play their strongest side they could possibly play to be honest, and it's a blow for every Spurs fan out there, but that's history.'
He also felt losing to such underdogs could be a blow in the rest of Spurs' season, as he added: 'If you lose away to Liverpool or Man United, that's a bit different than going to Sheffield United and I think that's piled on the pressure for the Milan game.
'Now you're going into this game where, if you get knocked out of that, there's no trophy coming to Tottenham again this season and if you want to keep your best players, you're going to have to be successful.'
Spurs go into Wednesday's Champions League clash needing to overturn a 1-0 deficit from the first leg.
They are currently drawing 0-0 on an evening that could go a long way to defining the rest of their season.