Hearts remain bottom of the Scottish Premiership after losing 1–0 to 10-man Kilmarnock at Rugby Park.
The hosts looked to face a tough task after defender Robbie Deyes was sent off inside the first 10 minutes for a hard challenge on Kenneth Vargas.
But Bruce Anderson’s spot-kick gave Killie the lead and they could have extended it, with Hearts goalkeeper Craig Gordon making great saves to stop Marley Watkins and David Watson.
Hearts hit the woodwork twice through Moussa Drameh and Yan Dhanda but they were disappointing against 10 men.
Kilmarnock manager Derek McInnes made two changes from the draw with Dundee United last time out, bringing on Bobby Wells and Watkins, while Craig Halkett and Drameh came on for Hearts in place of the injured Frankie Kent and the suspended Lawrence Shankland.
They were inches away from taking the lead after only a minute as Kilmarnock goalkeeper Robbie McCrory missed a corner, giving Drameh the chance to volley inside the post.
The home team escaped, but had no such luck later on as Des Vargas suffered a serious injury to his ankle.
Referee Don Robertson initially issued a yellow card to the Killie defender, which was upgraded to a red card after VAR Gavin Duncan sent him off the screen.
The match had had a busy start to the match for the referee and he was involved again after a quarter of an hour as he awarded Kilmarnock a penalty after James Penrice caught Joe Wright late in the corner of the box.
Anderson stepped up and put the ball to Gordon’s left to give Killie the lead.
Despite their numerical disadvantage, Kilmarnock should have doubled their lead in the 28th minute as Watkins was given a clean through but Gordon came out to make a crucial stop.
Watkins came close again in the 40th minute and attacked Fraser Murray’s cutback but Penrice made a vital block.
Hearts were sore after the red card and a low effort from Alan Forrest was easily saved by McCrorie as the first 45 minutes ended.
Kilmarnock had the first chance of the second half in the 48th minute when Brad Lyons stepped up and released Watson but the Killie substitute had his low effort well blocked by Gordon.
Kilmarnock had another chance in the 54th minute when Watkins cut the ball back for Liam Donnelly, whose deflected shot went wide.
Hearts still looked weak and boss Neil Critchley made four changes ahead of time, bringing on Liam Boyce, James Wilson, George Grant and Dhanda.
Wilson made an almost immediate impact as Cammy Devlin caught the Killie defense napping and cut the ball back but the young striker saw his shot blocked.
Kieran O’Hara replaced McCrory in the home goal at half-time and was eventually called into action in the 73rd minute, coming down to block Penrice’s low shot to safety.
Substitute Dhanda thought he had rescued a point for the visitors in stoppage time, but his curling shot came back off the crossbar as Kilmarnock secured a deserved victory.