St Johnstone opened up their Premier Sports Cup campaign with a 0-0 draw against Annan - and finished the game with nine men.
Perth centre-half Dan Cleary was shown a straight red by referee Don Robertson in the first half following an off-the-ball incident involving Tom Muir.
And then second half substitute Cammy MacPherson was sent off shortly before the full-time whistle for a challenge on Aidan Smith.
Neither side was able to make the breakthrough and that meant penalty kicks. Michael O’Halloran and Andy Considine were unsuccessful in the shootout to hand Annan the bonus point.
Manager Callum Davidson made just the one change from Saturday’s 3-2 friendly win against Cove Rangers and that saw Theo Bair - three goals in his last three games - replacing Stevie May.
Saints, as expected, enjoyed the bulk of the early possession and somehow did not take the lead on seven minutes.
A neat Considine pass sent Adam Montgomery into a promising position down the left flank. His square ball went all the way to the back post for Charlie Gilmour, who was unable to steer over the line from close range.
Ali Crawford soon went close with a powerful low strike from distance, again after neat build-up this time involving Melker Hallberg and Bair.
Annan continued to soak up the pressure and, just shy of the half hour mark, had a man advantage when Cleary was sent for an early bath.
After a quick discussion with his assistant, referee Robertson flashed a straight red following a melee in the midfield area of the pitch. Muir was the visiting player who ended up on the deck.
Sights of goal were rare for the remainder of the half and that trend continued in the early stages after the break.
Annan did begin to creep forward and went close to opening the scoring in the 59th minute when Scott Hooper, on the swivel, tried his luck from inside the box.
Montgomery produced an impressive piece of defending to throw himself in front of the ball and block.
Jamie Murphy and Graham Carey entered the action in the 66th minute, replacing Max Kucheriavyi and Crawford.
Both of the new arrivals made an immediate impact and linked up nicely, with Carey forcing a near post save before Murray Davidson’s follow-up was turned behind for a corner.
In the 75th minute, Hallberg and Gilmour made way for MacPherson and O’Halloran as Saints pushed for a late breakthrough. Stevie May also replaced Bair.
It was Annan, however, who should have nudged ahead on 80 minutes when, suddenly, Josh Galloway broke clear one-on-one at the angle with goalkeeper Elliott Parish. He struck the outside of the post.
Saints were reduced to nine men in the final minute when MacPherson was shown straight red for a late tackle on Smith. Perth boss Davidson was furious with the referee's decision.
The game went to penalties to determine who would take the bonus point. Murphy, May, Davidson and Carey found the net for Saints but O'Halloran and Considine couldn't.
Galloway stroked home the winning spot-kick from 12 yards.
