Ally McCoist was put on the spot by Celtic-daft talkSPORT colleague Alan Brazil ahead of Sunday’s derby at Parkhead.
The Rangers strike legend was offered a win against RB Leipzig at Ibrox next week and a place in the Europa League final.
But the condition was it had to be at the expense of a defeat against the Hoops in the lunchtime showdown in the east end of Glasgow this weekend.
McCoist was working for BT Sport in the RB Arena as Giovanni van Bronckhorst’s men went down to a late goal against the Bundesliga side.
They are still well in the tie ahead of the return at Ibrox next week but before that face a tough clash against Celtic, who would all but win the Scottish Premiership with a victory.
As Brazil invited McCoist onto his breakfast show alongside co-host Ray Parlour, he said: "We're heading over now to Germany, it's going to very difficult to have two disappointing results in the space of a few days, of course, with the big one on Sunday as well.
"I've got my box of tissues here, joining us now is Super Ally..."
And after discussing the game, Brazil said: “So the golden question Alistair, if I offered you defeat at Parkhead on Sunday but you beat Leipzig next week would you take it?”
McCoist was in a quandary and stuttered: “Oh my… oh. Can anyone hear me?”
Brazil laughed: “Only a couple of million…” before Parlour joked: “It’s breaking up. The line is breaking up.”
McCoist said: “Oh no, I can’t answer it. All I’ll say is that I went to the game praying the boys had an opportunity to give themselves 90 minutes to get to a European final and they’ve done that.”
Brazil said: “That means yes - you’ve just answered it. Thank you very much!”
But they agreed Gers impressed and McCoist said: “I could hear the disappointment in Giovanni van Bronckhorst’s voice.
“If we had lost the goal in the first five minutes and the game had finished 1-0 everyone would have been thrilled.
“It’s just the manner and timing of the goal but make no mistake - if someone had offered any Rangers fan 1-0 before the game you wouldn’t have their hand off.
“This is a team who scored three at the Etihad and have already beaten Man City. They went to Atalanta and won 2-0, beat Leverkusen in Leverkusen so you could argue they’re better away fro home.
“But you can’t deny it’s a great opportunity and the atmosphere at Ibrox will dictate they have to go forward and try and score but you have to keep the door closed at the back.”