Veteran musician Sir Cliff, 81, was pictured arriving on Monday dressed in a silver blazer with a red rose pinned to his lapel paired alongside a black shirt and striped tie.
TV presenter and author Osman was also spotted entering the All England Club on day one to watch the start of the action.
The 51-year-old was later seen in the royal box wearing a light blue blazer with a navy tie and white shirt.
Meanwhile, British astronaut Tim Peake sat in front of him in the box.
TV presenter Armstrong was also seated in the royal box on day one of the tennis tournament in south-west London.
The Pointless host could be seen wearing a cream blazer, blue shirt and a light-coloured tie as he took in the action from the sidelines.
Wimbledon kicked off on Monday with full-capacity crowds descending on the grand slam tournament for the first time in three years.
The 2022 championship marks the first time since 2019 that the grounds will be filled with up to 42,000 people every day since before the coronavirus pandemic.
The famous queuing will return as spectators from around the world camp out and line up for hours to buy on-the-door tickets every day.