Walter Smith may boast a managerial career spanning 17 years but the Rangers boss admits the next four weeks will represent his biggest challenge yet.
Smith embarked upon this season simply hoping to mount a stronger bid for domestic honours - instead he finds himself on the verge of an historic quadruple.
The visit of Fiorentina tonight in the last four of the UEFA Cup represents the biggest shock for Smith, who ended almost three years without silverware by claiming the CIS Insurance Cup last month.
Rangers are also favourites for the Premier League and are in the final of the Scottish Cup, and Smith admitted: 'This period that we are going through is probably the biggest test that I've had in my managerial career so far - and I'm not talking about fixture schedules and such.
'It is just a big test, as it is for all my players. We face 11 games and we've got to win them.
'Looking just at the short term, we've got these two games against Fiorentina, plus the Celtic game at the weekend, and they are huge, huge games for us.
'On a personal basis - I make no bones about it - I never thought we would get to the situation we are now in. I wanted to qualify for the Champions League because it brings in a level of finance that is necessary for the club, but I had no great illusions about doing a great deal this season.
'I'd just hoped that, if we stabilised, we'd pose a greater challenge to Celtic and do something in the domestic cups.
'So to still be fighting on all fronts, as we are at the moment, has surprised and delighted me.
'Obviously, when you make a decision to come back to a club, you hope there will be an uplift in terms of results.'
The SPL title was the priority at the beginning of the season but, with every hope of reaching the UEFA Cup final in Manchester next month, Smith refused to be drawn on which trophy is now the most attractive prospect.
'I don't think that you can prioritise,' he said. 'You want to try to win as much as you possibly can. I was always frightened of a situation where one (competition) could affect the other quite badly.
'So we've really just got to try in whichever particular situation we are in. I know it is an old managerial adage but we've just got to try as well as we can in each of the games as they come along.
'I've done that so far, and it has been good for us. That is how we should approach it.
'I mean, how do I prioritise? Do I leave players out for Fiorentina because we play Celtic on Sunday, but then lose against Fiorentina, and then go to Celtic Park with our best team and possibly lose there, which would affect both our league and UEFA Cup campaigns?
'We can't do that. We've just got to try to do the best that we can with the players that we have.'
Veteran defender David Weir will celebrate his 38th birthday next month but insists this season could eclipse everything else he has achieved in his career.
He said: 'We're in the semi-final of the UEFA Cup, the final of the Scottish Cup, we're still challenging for the league title and that's a great position to be in.
'Our destiny is in our own hands. We can make history. It could be a fantastic season and I'm sure at the start of the season if anyone had offered us this then we'd have grabbed it with both hands.
'There have obviously been injuries and suspensions which aren't ideal, but you're not going to be successful without problems or be successful without coming up against obstacles.
'So it's up to us as a team and as a squad to get over that and give it our best shot.'