Livi suffered penalty shootout agony as they tumbled out of the Irn Bru Cup to Welsh champions The New Saints for the second season in a row.
After Dylan Mackin had cancelled out Aeron Edwards’ opener for the home side, Scott Pittman missed the decisive spot kick as the Lions crashed out before the quarter finals for just the second time in five years.
The Lions made two changes from the side that claimed their first league win of the season against Morton eight days earlier as Nicky Cadden and Scott Robinson came in for James Penrice and Nikolay Todorov. Keaghan Jacobs started the match to become Livi’s all-time record appearance holder, surpassing Liam Fox’s 219 games for the club.
The Lions went into the clash looking to make amends for a disappointing 3-0 home loss to the same opposition last term but found themselves behind midway through the first half after a disappointing start as Edwards was left unmarked at the back post to head home a Jamie Mullan free-kick on 20 minutes before Livi began to settle into the game.
They enjoyed their best spell in the latter stages of the opening 45 minutes, including forcing five successive corner-kicks, but they were unable to drag themselves back on level terms.
Half-time: The New Saints 1-0 Livingston
The equaliser came on 64 minutes when substitute Dylan Mackin flicked a looping header from a Josh Mullin cross over the goalkeeper and into the far corner.
That led to the visitors, cheered on by the few dozen supporters who made the 500-mile round trip to Park Hall, controlling proceedings but they were unable to make their pressure count and find a crucial second goal.
New Zealand internationalist Greg Draper almost gave TNS the lead with his first action after coming off the bench, but his curling strike from just inside the box was deflected onto the crossbar, while centre-back Blaine Hudson should have done better with a header moments later.
At the other end, Livi looked dangerous on the attack but were unable to find a winner as the game ticked into the extra period.
With neither side really creating much, the game appeared destined for penalties for Nikolay Todorov was presented with a golden opportunity to fire Livingston into the third round draw.
The Bulgarian striker was teed up perfectly in the closing stages, but his effort rattled off the crossbar, while Mullin fired a shot at goalkeeper Paul Harrison with the final action of the contest.
Full-time: The New Saints 1-1 Livingston
That gave Simon Spender the opportunity to fire the Oswestry-based side into round three, but Alexander produced a stunning save to take it into sudden death.
Two successful penalties for both teams was followed up with Harrison rifling the ball into the bottom corner before Scott Pittman blazed high over the crossbar and send the Lions out of the cup in heartbreaking fashion.
Full-time: The New Saints 1-1 Livingston (The New Saints win 6-5 on penalties)
TNS: Harrison, Spender, Rawlinson, Routledge, Fletcher (Draper 80), Parry (Brobbel 63), Hudson, Mullan, Roberts (Pryce 81), Holland (Sergeant 112), Edwards
Subs not used: Jones, Leak, Cieslewicz
Goals: Edwards (20)
Penalties: Mullan, Draper, Brobbel, Sergeant, Spender, Rawlinson, Routledge, Harrison
Livingston: Alexander, Gallagher, Halkett, Lithgow, Mullin, Byrne, Pittman, Jacobs (De Vita 60), Cadden (Longridge 71), Mullen (Todorov 105), Robinson (Mackin 60)
Subs not used: Maley, Knox, Carrick
Goals: Mackin (64)
Penalties: Mackin, Todorov, Halkett, Lithgow, Gallagher, Longridge, Mullin, Pittman
Referee: Robert Harvey
Match Report: Andy Crawford
Photos: Rae Irvine