During the 2000s, O'Connor and her sport pony Theodore O'Connor, nicknamed Teddy, gathered a large following as he competed and won against much larger horses. The pair finished third at the 2007 Rolex Kentucky Three Day and sixth at the same event in 2008. At the 2007 Pan American Games, O'Connor, riding Teddy, won individual gold and assisted the US squad to a team gold. In 2008, short-listed for the US eventing team at the 2008 Olympic Games, Teddy suffered a catastrophic injury and was euthanized. The United States Equestrian Federation (USEF) issued a press release that stated "Seeing was believing with ‘Teddy’ as it seemed impossible to imagine that a pony of his size could do his job with such tremendous ease." In September 2009, O'Connor suffered a broken shoulderblade in a motorcycle accident. She was out of competition for five weeks, during which time her main mount, Mandiba, was ridden by fellow US eventer Phillip Dutton. Between 2010 and 2012, O'Connor continued her successful career, riding to multiple top-ten finishes, and several wins, at CCI2–4* events, aboard a number of horses. On October 6, 2012, O'Connor fell while competing at the Morven Park Fall Horse Trials in Leesburg, Virginia. She suffered a burst fracture of her T4 vertebra and a compression fracture of her T5 vertebra. After one of the vertebra shifted, she underwent surgery on October 18. In June 2013, it was announced that during the remainder of her recovery, Phillip Dutton would again take over as the rider of her top horse, this time 2012 Olympic mount Mr. Medicott. When not competing, O'Connor serves as a member of the USEF's Board of Directors and as an active member of the United States Eventing Association's (USEA) Instructor Certification Program. In 1995, O'Connor's horse Biko was named "The Chronicle of the Horse's" Eventing Horse of the Year, and in 1996, O'Connor was named the journal's Eventing Horseman of the Year, in combination with her husband, David. In 1999, Biko was honored as the USEA's Horse of the Century, and in 2006, was inducted into the organization's Hall of Fame. In 2007, O'Connor's pony Theodore O'Connor was named "The Chronicle of the Horse's" Overall Horse of the Year and Eventing Horse of the Year, as they called him the "horse world's most adored underdog".