Airdrieonians secured a stunning cup victory on 30 August 2008, beating Hearts 0‑0 after extra‑time and prevailing 4‑3 in the penalty shoot‑out at Tynecastle. The win sent the First Division side through to the next round of the Co‑operative Insurance Cup.

Both teams struggled to find the net in 120 minutes, with Airdrieonians’ Kevin McDonald receiving a second yellow and being sent off in the 107th minute. Hearts pressed for a breakthrough, but goalkeeper Stephen Robertson kept a clean sheet, denying David Obua’s spot‑kick in the shoot‑out. Airdrie’s Scott McLaughlin converted the decisive fourth penalty, sealing the triumph.

Stephen Robertson was the standout, making key saves in regular time and the penalty shoot‑out. Scott McLaughlin kept his composure to score the winning spot‑kick, while Paul Di Giacomo forced a memorable early chance that rattled the crossbar. Hearts’ Christos Karipidis and Jamie Mole were denied by Robertson’s reflexes.

Hearts manager Csaba Laszlo lamented the missed opportunities, noting the team played “about 10 minutes against 10 men” and must now focus on the Scottish Cup and league. Airdrieonians boss Kenny Black praised his squad’s mental strength, joking about the “50,000 a man” pressure on penalty takers and lauding the goalkeeper as one of the division’s best shot‑stoppers.

The club now looks ahead to its upcoming league clash, with the next fixture scheduled as an away game against Alloa Athletic on 7 November 2026. The victory provides momentum, but the squad must maintain focus as the season progresses.

Match details: Hearts lined up with Kello, Karipidis, Zaliukas, Berra, Lee Wallace, Mikoliunas (Cesnauskis 73), Stewart, Jonsson, Obua, Kingston (Ksanavicius 70), Mole (Nade 93). Airdrieonians fielded Robertson, Smyth, Bobby Donnelly, Nixon, Hazley, McDougall (Smith 83), McKenna, McDonald, Cardle (Brown 80), Di Giacomo (Lynch 78), McLaughlin. Attendance was 6,844, and referee E Smith officiated.