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The Benfica manager is familiar with Osmand from their shared time at Fulham, where the striker was developing in the youth ranks before joining Celtic in 2025.
Silva said: "I remember the goal and it’s nice to see him be himself. He’s a very good boy who took a decision in that moment to go from England to Scotland and to sign for a big club."
Osmand was still playing youth football at Fulham before deciding to make the switch to Celtic, and Silva believes taking the opportunity to play at senior level represented a significant step in his career.
He added: "Of course he’s a very young player and a player who wasn’t playing in the Fulham first team. He was playing for the Under-23 team.
"Going from that spot to playing for a club that was playing to be champion in Scotland was a big step.
"It was important for him to play senior football."
Osmand went on to score the goal which sealed Celtic’s Premiership title last season, rolling the ball into an empty net against Hearts.
And while Silva retains plenty of affection for his former player, there will be no room for sentiment when Benfica meet Celtic in the Europa League. He said: "It’s nice to see him play.
"It’s important we don’t give him a chance to show up tomorrow."