This cup win kick-started an unbeaten run of 13 games as Inverness went from lingering around the lower echelons of the table to mid-table. However, despite a late push, an injury-time equaliser in the final home game of the season against Dunfermline meant ICT narrowly missed out on the promotion play-offs by just two points, finishing in 5th place despite winning 3–0 away to Greenock Morton on the final day, which would've confirmed a play-off slot had Dunfermlne either drawn or lost to Dumbarton. In August 2018, the club was saddened to learn of the death of ex-player Alan Hercher at 52 years of age. He was the club's first captain, goalscorer and hat-trick scorer – in their first league game against Arbroath. In tribute, a minute's silence was held at Inverness' first home game of the 2018–19 Scottish Championship season against Ayr United which ended in a 0–0 draw. Come the new year, Inverness were doing better than they had the previous season, sitting in the play-off spots despite drawing nearly every game. The club beat rivals Ross County to progress into the quarter-finals of the Scottish Cup before making the semi-final after a last gasp winner from Aaron Doran against Dundee United. This was the 4th semi-final appearance for the club, after appearances in 2002–03, 2003–04 and 2014–15. They played Heart of Midlothian, but were unable to proceed to the final, as they were defeated 3–0. By the end of the season, Inverness had secured a play-off spot, after leapfrogging Ayr United into 3rd place. In the quarter-finals, Inverness defeated Ayr, winning 3–1 in the first leg, and drawing 1–1 in the second, securing a comfortable 4–2 aggregate win. However, the joy was short-lived after facing Dundee United in the semi-finals. In the first leg, at home, they fell to an unfortunate 1–0 loss while down to 10 men after Liam Polworth was handed a straight red for an apparent high foot on Mark Connolly while making a clearance. Inverness went to Tannadice with heads held high hoping to overturn the 1–0 deficit, but hope began to fade after United were awarded and scored a controversial penalty just before half time. The penalty was conceded by a Brad McKay handball, after it deflected off his heel.