Aberdeen and Kilmarnock are through to the third round of the CIS Cup while Inverness and Airdrie progressed on penalties.
Former Hearts midfielder Kenny Black came back to haunt his old side as First Division strugglers Airdrie United sprang a major surprise by knocking their hosts out of the cup on penalties.
Manager Black's 10-man Airdrie side won 4-3 on penalties to progress to the third round and inflict an embarrassing defeat on new Hearts boss Csaba Laszlo.
Former Scotland Under-21 goalkeeper Stephen Robertson denied Lee Wallace and David Obua with saves in the shoot-out - the last from the Ugandan - with Darren Smith the only man to miss for Airdrie.
Hearts, for all their possession, lacked a cutting edge even after Airdrie lost Kevin McDonald to a red card in extra-time.
As Airdrie celebrated, boos echoed around the stadium at the finish as Hearts joined Edinburgh rivals Hibernian as unlikely early cup casualties.
Inverness made it through to the third round - but only after Angus side Arbroath forced their SPL opponents all the way to penalties.
Ian Vigurs netted the decisive spot-kick in a thrilling encounter as Paul Tosh and Paul Lunan both missed for the home side to see them crash out 4-2 on penalties.
That came after Caley, reduced to 10 men after an extra-time red card for Andy Barrowman, were twice ahead through Vigurs and Garry Wood only for Tosh and Barry Sellars to cancel out their strikes.
Kilmarnock booked their place in the third round following a hard-fought victory over Brechin.
The Second Division side had goalkeeper Craig Nelson to thank for keeping Killie at bay in the first half but he could not produce more heroics after the break to deny Frazer Wright.
Killie's tensions were eased on 65 minutes when a stunning shot from Craig Bryson made sure of their place in Monday's draw.
Chris Maguire grabbed the winner as Aberdeen scraped past Ayr United.
The Pittodrie side could have knocked the stuffing out of their hosts early on when Jamie Smith's corner found the head of Derek Young, who glanced across goal and wide when he really should have scored.
Aberdeen settled the contest five minutes before half time when Charlie Mulgrew supplied a curling ball from the left and Maguire beat Stephen Grindlay to the ball to stab home from a few yards.
