Drawing for Surrounded Islands, Christo and Jeanne-Claude

The Bulgarian artist Christo, who works with his wife Jeanne-Claude, gained acclaim for surrounding 11 islands off Miami with polypropylene. One of his preparatory drawings for the Miami work was damaged in transit, when a packing company drove straight through the work with a forklift truck. The piece now sits in the offices of its London insurer, Axa Art, as Christo prefers damaged pieces not to be sold.

Le Rêve, Picasso

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Las Vegas casino mogul Steve Wynn had just agreed a £74m sale for his Picasso, Le Rêve (The Dream), when he stumbled into the canvas in 2006, busting a hole in it with elbow. The painting hung in Wynn's office alongside a Matisse and a Renoir, and he was showing it to guests when he backed into the canvas, leaving a two-inch tear. The sale fell through.

Wall Relief, Craig Kauffman

When, in 2006, American art dealers and collectors shipped the exhibition Los Angeles 1955-1985: the Birth of an Artistic Capital to the Pompidou Centre in Paris, they imagined the many seminal works would be well looked after. In fact, two were damaged – an 8ft polyester resin bar by Peter Alexander dropped off a wall before launch night, and Craig Kauffman's Untitled Wall Relief, which had survived three earthquakes in LA, soon met the same fate.

Qing vase

A clumsy visitor to Cambridge's Fitzwilliam Museum tripped over his shoelace and fell down a staircase, taking a set of 300-year old Chinese vases with him. The Qing porcelain, dating from the 17th century, was among the museum's most valuable pieces. The painstaking clean-up took two and a half days as all the pieces needed to be saved. Restoring the vases (one of which weighed 45kg) was a six-month job. The visitor was arrested but released without charge, and the vases are now back on display.

Recreation of First Public Demonstration of Auto-Destructive Art

Gustav Metzger A plastic bag of discarded paper thrown away at Tate Modern in 2004 turned out to be part of a copy of a 1960 work showing the "finite existence" of art. Ironically, Metzger was a founder of the Auto-Destructive movement.

House, Rachel Whiteread

In the autumn of 1993 Whiteread rendered a Victorian terraced house in concrete on an east London site where the road had already been demolished by Tower Hamlets council. The work won her the Turner Prize and was described in this newspaper as "one of the most extraordinary and imaginative sculptures created by an English artist", but the council still demolished it a year later.

Painting-By-Numbers, Damien Hirst

To mark the opening of his 2001 exhibition of Painting-By-Numbers, Hirst assembled empty beer-bottles, overflowing ashtrays and paint tins into a gallery installation. He intended the construction to resemble a messy artist's studio. When the cleaner arrived after the launch, he cleared it all away. The work was retrieved from the dustbin. Hirst declared it "very funny".

Mantegna Frescoes, Andrea Mantegna

The Allied air raids on Italy in 1944 were intended to cripple industrial centres. On the way back to base, one pilot dropped his bombs over Padua, striking the Church of the Eremitani and destroying a set of 15th-century frescoes.

Venus de Milo

The sculpture of Venus or Aphrodite stands in state in Paris's Louvre, mesmerisingly beautiful despite her broken form. She was discovered by a Greek peasant on the island of Milos in 1820, broken into two large pieces, an apple in her left hand. As soon as French naval officers recognised the historical significance of the ancient sculpture, they set about hauling the marble bulk off the island. A fight broke out as Venus was dragged across rocks to a waiting ship and both arms were broken off. The exhausted sailors refused to retrace their steps and search for the body parts, so the goddess's left arm remained cut off at the shoulder and her right at breast level.

Pulp Fiction, Banksy

Last April, months after a Banksy had sold for £102,000 at Sotheby's (a record for the artist), Transport for London painted over his Pulp Fiction mural in London's East End. The piece, which depicted John Travolta and Samuel L Jackson clutching bananas, was considered graffiti. One critic remarked that this would raise Banksy's stock and soon after, his Space Girl & Bird piece fetched £288,000, 20 times the estimate. By October, Brad Pitt and Angelina Jolie spent £1m on works by the "guerrilla artist".

Vase with Five Sunflowers, Van Gogh

Van Gogh's 1888 painting was part of the Sunflowers series. Still Life: Vase with Five Sunflowers was shipped to Japan in 1920 and bought by Koyata Yamamoto, who stored it in a bank vault, where the piece was burnt in a fire ignited by an American air raid in 1945.

The Last Supper, Leonardo da Vinci

Leonardo da Vinci painted his 15th-century masterpiece The Last Supper on wet plaster, using a mix of egg yolks and vinegar. Within a few years the Milanese mural was flaking, and it was pronounced "ruined" half a century later. When a curtain was hung across the work in the 18th century, it trapped moisture close to the surface and scratched the flaking paint when it was pulled back. The most recent restoration effort lasted 21 years.