Rangers fell to a 2-1 defeat against Ajax in their first public pre-season friendly.
Tom Lawrence was on target for the Ibrox club but his free-kick strike was rendered a consolation.
Goals from Kian Fitz-Jim and Branco van den Boomen were enough to see Ajax triumph at home of WHC Wezep - De Mulderssingel, Wezep, Netherlands.
Jack Butland prevented an early lead for Ajax with a superb diving save from Chuba Akpom in the early stages.
But the Eredivisie side struck first after 26 minutes when a quick free-kick caught the Rangers defense off-guard.
Butland raced out his goal to slide for the ball but Fitz-Jim was on hand to poke into an empty net following the goalkeeper's attempt to smother the ball.
Rangers would level just seven minutes later, though, with Lawrence on target direct from a free-kick to find the bottom corner and restore parity.
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On 39 minutes, Ajax retook the lead with a free-kick of their own as Van den Boomen's effort squirmed under Butland and into the bottom corner.
Shortly before the break, Rangers would be dealt an injury blow with Nico Raskin forced off injured and replaced by Connor Barron.
Rangers would push for a leveller in the second half with Scott Wright going close only to be denied by the Ajax keeper.
A fluid move ten minutes from time saw Wright again presented with a sight of goal but he was denied by another smart stop.
Liam Kelly - on for his first minute as a Rangers player again made two big stops in the closing minutes to keep the score at 2-1.
