As a former Hearts and Celtic player, Alloa Athletic manager Paul Hartley used to torment Rangers on a regular basis.
On Saturday, however, he faces arguably the biggest challenge of his managerial career so far as he takes his Division Two title hopefuls to Ibrox to face Division Three leaders Rangers on Scottish Cup duty.
The rookie gaffer led the Wasps to the Third Division title at the first attempt last season – something that Ally McCoist might like to ask him about when they meet for the post-match glass of wine on Saturday evening – and he has guided them to second position in Division Two this season, with back-to-back promotions still very much on the cards.
But with Rangers boasting a team of stars that most fans feel would still grace Division One or possibly even the SPL, this match could be a step too far for Hartley’s underdogs.
The Gers have been far from convincing on the road this season, only securing their first away win at Clyde last Sunday, but at Ibrox they have been generally excellent, winning seven out of nine matches so far.
Wednesday’s defeat to Inverness in the Scottish Communities League Cup was their first reverse on home soil this campaign. They are yet to drop a single point in a home league match and beat SPL side Motherwell en route to their quarter-final tie with Terry Butcher’s Highlanders.
Hartley, though, need look no further than his own league for inspiration on how to pull off a cup upset at Ibrox.
Earlier in the season, Division Two leaders Queen of the South knocked Rangers out of the Ramsden’s Cup on penalties after holding them to a 2-2 draw in 90 minutes. While there is no prospect of extra-time and penalties this time around, there is the possibility of a money-spinning replay back at Recreation Park.
Bwin have priced a draw on Saturday at 35/4 and this outcome might have a few takers hoping for another Rangers off-day to boost their coffers.
Anyone who believes Hartley can inspire an unlikely away victory will get very tempting odds of 33/4, while those who prefer to play it a bit safer will only get odds of 3/25 on a Rangers victory.
Perhaps the best bet, however, could be backing Alloa to score at 5/4. New customers who register with bwin online qualify for a free £20 bet and using that to back the visitors to get on the scoresheet will return £45 if successful.
While they might not have enough in the tank to beat Rangers over 90 minutes, nine sides out of 17 to face Rangers this year have scored – so it must be worth taking a chance on Hartley’s men following suit on Saturday at odds against.