At the 2003 Pan American Games, O'Connor took an individual silver medal, riding Joker's Wild. During the 2000s, O'Connor and her 14.1 hands (57 inches, 145 cm) 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.

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