The first half of Champions League play-off fixtures concluded on Tuesday.

Here’s what we made of the action.

A real thriller in Lisbon

📸 Gualter Fatia – 2025 Getty Images

The Champions League’s play-off round has already delivered some thrilling spectacles but Benfica’s five-goal thriller with Monaco will take some beating.

One goal separated the teams heading into their return encounter at the Estádio da Luz as both aimed to set up a last-16 meeting with either Liverpool or Barcelona.

A below-par hosts saw their slender advantage cancelled out several times by Les Monégasques in a contest which was truly end-to-end until the closing stages.

No sooner had Bruno Lage’s men fallen behind on the night for a second time that Orkun Kökçü delivered a swift rebuttal to secure their passage.

Whichever of the league phase’s top two that As Águias draw on Friday, they will need to produce another monumental effort to try and reach the quarter finals.

Milan’s UCL sheen fades further

📸 MARCO BERTORELLO – AFP or licensors

The Champions League remains synonymous with Milan.

Others have won it more recently, including their local rivals Inter, but only Real Madrid can lay claim to greater success in the competition than the Serie A giants.

But European nights are not what they once were for the Rossoneri as they crashed out at a sparsely populated San Siro to Feyenoord in a 2-1 aggregate reversal.

Sérgio Conceição’s side started promisingly with Santi Giménez’s opener against his former employers with barely 40 seconds on the clock in their second leg clash.

Once Theo Hernández received his marching orders, however, the visitors scented blood and pulled level on the night to claim their first last-16 spot in 25 years.

Club Brugge are the new fairytale

📸 ALBERTO PIZZOLI – AFP or licensors

Move over, Atalanta – there’s a new European fairytale in town.

Gian Piero Gasperini’s men have been one of the continent’s real feelgood stories in recent years, culminating with last season’s Europa League final success.

Yet La Dea must now take a back seat after missing out on a spot in the last 16 to Club Brugge, who finished dead last in qualification from the league phase.

Not only did the Blauw-Zwart produce a first-half blitz in Bergamo which gave them a commanding 5-1 aggregate lead at the interval, but they made further history.

Teenager Chemsdine Talbi’s brace saw him become both the youngest Belgian player to net twice as well as the fourth-youngest overall in the competition’s history.

Kompany’s Kane gamble almost backfires

📸 Matthias Hangst – 2025 Getty Images

Bayern Munich fans feared the worst when Harry Kane was a notable absentee from their training session ahead of their finely poised return leg with Celtic.

The England captain’s omission was downplayed by his manager Vincent Kompany, who publicly diagnosed it as “nothing serious” other than additional recovery time.

But the Bayern boss clearly spoke too soon as Kane was withdrawn at the interval in the Allianz Arena with his side still far from out of the woods in their play-off tie.

When Nicolas Kühn returned to haunt his former employers with a swept finish to draw the Bhoys level, it appeared ominous for the Bundesliga’s runaway leaders.

Fortunately for Kompany, Alphonso Davies cropped up deep in added time to ensure his side progressed despite a valiant effort from their visitors.

📸 Alex Grimm – 2025 Getty Images