A NIGHT of astonishing drama at Petershill Park ended with goalkeeper Lee Alexander saving three Brondby penalties in the shoot-out which decided the last 16 tie. It capped a fine personal performance and also one by her side, who were outplayed in the opening 45 minutes but ended the game far the stronger.

Jo Love scored the winning penalty to make it three out of four for her side and a margin of 3-1 in front of a sell-out attendance of 800 at the small Glasgow ground. City will go into the quarter final draw a week on Friday for the second time in their history.

Scott Booth made two changes to the side which won in Copenhagen, Megan Foley replacing the suspended Leanne Crichton midfield, and Jenna Clark coming in at centre back for the injured Eilish McSorley.

The opening five minutes were dramatic and set the tone for a fiercely contested tie. The evening might have taken a very different course had City scored with less than 120 seconds on the clock. Hayley Lauder delivered a low cross from the right but the in-rushing Foley couldn't quite get the touch which would have opened the scoring.

Instead it was Brondby who almost took the lead – and then did. The first effort, in the fourth minute was from Linnea Svensson and Lee Alexander had to be at her best to block the shot with her legs.

The early goal which Booth had warned against came just 60 seconds later. Emillie Henrikson sent over a perfectly judged cross from the right where it was met at the far post by Brondby's best player, Nanna Christiansen. Her header went across Alexander and into the other corner.

The Danes dominated possession for the rest of the half with City not finding the same space to counter-attack as they had done so effectively on the much bigger pitch at Brondby Stadium. They would have doubled their lead midway through the half, but Scotland keeper Alexander made another fine save, this time from Nicoline Sorensen's closer range volley.

The home side's best opportunity to equalise came after 34 minutes. Some excellent close passing among three players in the centre of the pitch led to Clare Shine being released down the right. She cut it back into the path of Sam Kerr, but the midfielder's attempt was blocked for a corner by Linnea Svennson.

As with the events before the first goal, it took Brondby just three minutes to score one themselves. A one-two on the edge of the home box saw the ball released to Frederikke Lindhardt, and she squeezed a shot across Alexander to level the tie on aggregate.

A long range shot from Rachel McLauchlan gave City some encouragement at the start of the second half, but Alexander again came to her side's rescue with another important stop. Again it was from Sorensen, who wriggled her way into the box but was thwarted by the goalkeeper's body.

Brondby missed an even better chance to take the lead in the tie for the first time following an error by McLauchlan. It gave Lindhardt possession with only Alexander to beat, but yet again the goalkeeper proved up to it, sticking out a leg to prevent the goal-bound shot.

For all the momentum had swung in Brondby's favour, the longer the second half progressed the more the home side were taking the game to their visitors. With less than 20 minutes remaining they came very close to scoring, but Shine was just beaten by Brondby goalkeeper Katrine Abel after being set up by Nic Docherty and Lauder.

For all that City had evened up the contest, the Danes should have sealed their place in the quarter finals five minutes from the end. Once more it was Sorensen through on Alexander and once more the goalkeeper's reactions saved her side.

Brondby then survived a strong penalty claim after Foley's shot was blocked by an arm in the box, leaving the game to go into extra time.

The best chance of the first half of extra time fell to the home side and they were very unlucky not to score. Kirsty Howat was fouled just outside the box, Leanne Ross took the free kick and it was headed against the underside of the bar by Clark. City then had another penalty claim denied as Kerr's follow up appeared to be handled.

City were again the better side in the second period of extra time added on and came close again with another Ross free kick near the end – but the game was settled by penalties with Alexander again outstanding and Jo Love scoring the one that settled the tie.