A claimant received £6,000 after the bench fell on their head in 2010, while another person received £1,250 after suffering pain when the changing unit fell on to their head at a leisure centre.
The information, obtained from a Freedom of Information request, shows the borough has also paid out for damage to clothing caused after it became caught on wires and the edge of a sign.
Payouts in the 2012 calendar year amounted to more than £13,000, while £34,911 was paid out to a single claimant in 2010 after they sustained a fracture after tripping over an uneven footway while jogging on Bouldish Farm Road in Ascot.
Cllr Simon Dudley, cabinet member for finance, said sometimes the borough is at fault and must pay up but it is working hard to stamp out 'vexatious claims'.
"We are performing far better than the average local authority," he said.
"We are not interested in encouraging the compensation culture."
The borough receives about 150 claims a year, of which about 10 per cent are successful.
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Police officers can be seen at Ten Pin Bowling in Maidenhead tonight following an incident earlier today.