The Portugal international, who was Newcastle star Sandro Tonali’s team-mate at San Siro until his £53million summer switch to Tyneside, completely fluffed his lines with only goalkeeper Nick Pope to beat after attempting an audacious flick at the end of a stunning 34th-minute run and only succeeded in tripping himself.
Pope will feel he had already earned his slice of good fortune after making five first-half saves in the space of six minutes to pave the way for a 0-0 draw which banked a priceless first point for the Magpies’ Group F account on their return to European football’s top table after an absence of 20 years.
For the seven-time winners, who were thrashed 5-1 by derby rivals Inter Milan on Saturday, there was no salvation on a night when they created enough chances, but were unable to take any of them, much to the annoyance of the locals among a crowd of 65,695.
Pope had to come to Newcastle’s rescue five times in quick succession after Dan Burn, one of two Geordies in Eddie Howe’s starting line-up, allowed the ball to run across him, forcing Sven Botman to make a hurried clearance.
Midfielder Tommaso Pobega pounced on the loose ball to test the keeper from distance and Pope had to react swiftly to repel Samuel Chukwueze’s header as the ball was recycled before denying Olivier Giroud from point-blank range with his defenders unable to keep the red and black shirts at bay.
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The England international then tipped away Rade Krunic’s raking drive and turned Giroud’s 19th-minute header over the bar after he had been left criminally unmarked from the resulting corner.
Ruben Loftus-Cheek blazed over from long range after once again bursting through the black and white cover with Howe’s men under sustained pressure with Tonali, Bruno Guimaraes and Sean Longstaff struggling to exert any control in midfield.
Longstaff was appealing in vain for a 31st-minute penalty after going down under Leao’s challenge and as Spanish referee Jose Sanchez waved play on, Theo Hernandez broke down the left and crossed for Giroud a the near post, only to see him fire wastefully wide.
Leao should have put Milan ahead 11 minutes before the break when he carved his way into the penalty area and past three lunging tackles to go one-on-one with Pope, but inexplicably tried to back-heel the ball home from six yards and simply fell over with Jacob Murphy hacking Pobega’s follow-up off the line.
Murphy mustered the Magpies’ first attempt with a curling 41st-minute shot which flew well wide after Kieran Tripper, Longstaff and Alexander Isak had combined well, but there was a measure of relief when the half-time whistle sounded with the score still at 0-0.
Tonali blasted a shot straight at defender Malick Thiaw and Murphy blazed high and wide as Newcastle returned determined to make an impression as an attacking force.
Milan’s build-up play was patient, but the holes which had appeared in the visitors’ defence at regular intervals before the break remained stubbornly closed after it.
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Howe made his move with 27 minutes remaining when he sent on Callum Wilson and Miguel Almiron for Anthony Gordon and Murphy, although Pope had to field a stabbed shot from substitute Tijjani Reijnders within seconds.
Frustration grew among the Rossoneri ranks with Hernandez chancing his arm from all of 35 yards only for Botman to thump his attempt away, although Tonali was applauded warmly by the home fans when he was replaced by Elliot Anderson with 18 minutes remaining.
Leao might have atoned for his first-half blunder when he dived to meet Alessandro Florenzi’s 74th-minute cross, but he sent his header over Pope’s crossbar, and a late flurry by Milan was met with stern resistance as the game ended goalless, but only after substitute keeper Marco Sportiello had tipped Longstaff’s stoppage-time pile-driver over.