Montgomerie met his first wife Eimear Wilson, from Troon, when he was a good amateur and she was a promotions assistant. She was a 17-year-old law student at Edinburgh University and a spectator at an amateur championship in Nairn, at which Montgomerie destroyed the field. The couple had three children (Olivia, Venetia, and Cameron), and lived in Oxshott, Surrey. In 2002, Eimear gave Montgomerie an ultimatum to choose between golf and marriage, resulting in Montgomerie spending 10 weeks alone before they agreed to try again.