[2] Kilmarnock were seeded for the group stage draw of the League Cup and were drawn to face rivals Ayr United along with Dumbarton, Clyde and Annan Athletic.

In their opening fixture, Kilmarnock lost their first Ayrshire derby for 18 years after Andy Geggan scored the only goal at Somerset Park.

[4] There was a question over whether Celtic should have been awarded a penalty after 13 minutes when Jonny Hayes appeared to dive in the box but it made little difference as they eased to a 5–0 win and knocked Kilmarnock out.

[6] Kilmarnock were originally scheduled to play their first away match on 12 August 2017 against Heart of Midlothian but the fixture was reversed due to the redevelopment of Tynecastle Stadium.

The rearranged Hearts tie, due to be played on 5 November 2017, was subsequently switched to Murrayfield Stadium because the redevelopment works had taken longer than initially scheduled.

[13][14] With new manager Steve Clarke watching from the stand, Kilmarnock claimed their first league win of the season with a 2–0 victory at Firhill Stadium against fellow strugglers Partick Thistle.

Daniel Candeias stepped up but his effort was saved by Killie keeper Jamie MacDonald and Kilmarnock broke up the other end with former Rangers midfielder Chris Burke netting the equaliser.

The scoreline may suggest a Halloween horror show for Clarke's men but the home side were extremely unlucky - creating 16 scoring opportunities in the match - as a clinical Hibs recorded a 3–0 win.

Hamilton claimed that the match was "swept away by nature" after snow - which had been left on the pitch overnight - had frozen leaving the artificial surface unplayable.

[30] The draw for the fourth round was made on Monday, 20 November 2017[31] and Kilmarnock were drawn at home to fellow Premiership side Ross County.

After conceding an early goal at Pittodrie Stadium, Killie battled back and earned a replay at Rugby Park thanks to a Kris Boyd penalty.