An early bath for Michael Devlin after just 3 minutes set the tone for the match as Aberdeen were forced to play on the counter against a well organised Kilmarnock side who produced two moments of quality to win the match thanks to goals from Brophy and Stewart.
Derek McInnes made three changes to the side which took a point at Easter Road last week. Shay Logan and Niall McGinn were recalled to the starting line-up in place of Dominic Ball and Frank Ross who dropped to the bench. Max Lowe made his Aberdeen debut replacing Tommie Hoban who missed out through injury.
The Dons were put on the backfoot almost immediately when they were reduced to ten men in the 3rd minute of the match. The dismissal came when Brophy flicked the ball past Devlin 40 yards from goal, the touch left the striker with plenty to do but the referee decided to produce a red card for a last man challenge after Devlin pulled Brophy back. From the free-kick Lewis had to be alert to deny Brophy with a fine save.
The red card forced a change and Ball replaced Gleeson who had barely had a chance to get a touch of the ball. The Dons had to regroup quickly with all the pre-match plans out the window and settled into a 4-4-1 formation.
Brophy managed three attempts on goal in the opening ten minutes and the third almost ended in a spectacular goal but thankfully his 30-yard strike cannoned off the angle between post and bar before heading out to safety.
After a frantic fifteen minutes The Dons began to exert some pressure on Kilmarnock high up the park which offered plenty of encouragement to the home support but they were unable to test MacDonald.
Power received a yellow card after a great energetic run from Shinnie who had broke up the play inside his own half before linking up with May. The captain then spun away and was pulled back by Power 40 yards from the Kilmarnock goal.
In the 27th minute Lewis was called into action when a through ball from Tshibola to Burke got inside Lowe, the winger tried to skip past the keeper but Joe did well to thwart him with a brave interception.
On the half-hour mark Ferguson caught Tshibola in possession on the edge of the area and the Kilmarnock man retaliated with a poor challenge which cost him a yellow card. From the free-kick McGinn looked to have produced a moment of real quality but it was matched by a magnificent save from MacDonald who moved quickly to tip the ball over the bar.
Just a couple of minutes before half-time Shinnie was adjudged to have fouled Stewart 30 yards from goal. The Dons were collectively enraged by the decision, primarily because it looked as though O'Donnell had handled the ball in the build-up. The free-kick was taken by Brophy who looped the ball over the wall and into the bottom corner of the net leaving Lewis with no chance.
It was a great strike but the manner of the decision to give the free-kick caused uproar inside Pittodrie, particularly in the Dons dugout and Craig Thomson took the decision to have a word with Derek McInnes, a move which the Red Army were quick to voice their disproval of.
After a thoroughly frustrating half The Dons headed into the half-time break one goal behind. When they re-emerged for the second half Aberdeen retained the same shape and personnel to try and overturn the deficit.
Shinnie won a free-kick in the 49th minute when he was brought down by Findlay on the touchline. From the free-kick Logan got up at the back post but his header ended up over the bar.
In the 54th minute Kilmarnock had a free-kick of their own 25 yards from goal after Ferguson fouled Jones and received a yellow card for his trouble. There was no repeat of the first half as Brophy's strike was deflected over the bar. Moments later the striker picked up a yellow card for timewasting.
The striker continued to cause problems for The Dons as he got in behind the defence once again and unleashed a powerful strike towards goal which Lewis tipped round the post. With 35 minutes remaining Aberdeen were struggling to get going with Kilmarnock using their extra man well in the opening stages of the second half.
The supporters were offered a bit of encouragement when a long diagonal from Logan fell into the path of May, the striker did well to get the ball under control and unfortunately dragged his shot wide of the post.
With half an hour remaining McGinn was replaced by Cosgrove as The Dons looked to go a bit more direct and provide additional support to May up front.
The Dons had half a chance to get back into the game when Mackay-Steven broke down the right and clipped the ball into the area but it didn't fall kindly for Cosgrove. From that attack the ball was cleared up the pitch for Stewart to collect on the halfway line, he turned Considine quickly and began an unstoppable run towards goal before clipping the ball over Lewis and into the back of the net with twenty minutes of the match remaining.
Kilmarnock almost made it 3-0 when Jones skipped away from Shinnie down the right before attempting to slide the ball past Lewis at the far post but the goalkeeper got down well to turn it round the post. With 25 minutes of the match remaining May was replaced by Anderson.
In the 77th minute Anderson created a half chance for Cosgrove when he received the ball to feet on the edge of the area before laying the ball off for his strike partner. Cosgrove could not direct the ball towards goal with his left foot.
Kilmarnock were frustrating Aberdeen as the clock ticked towards full-time and Graeme Shinnie picked up a yellow card after contesting some perceived time-wasting a bit too vigorously.
Logan followed the skipper into the book picking up a yellow card of his own after losing possession inside his own half. As the 90 minutes drew to a close Anderson had a half chance after Cosgrove won the ball in the area but he couldn't keep the volley down and on target.
The youngster had another half chance as the board for added time was being prepared but this time he couldn't keep the volley down on his right foot. Two minutes of additional time were to be played with the remaining home supporters staying in hope rather than expectation as the visitors ran out winners. A tough day at the office for The Dons.