He finished second aboard Miami in the 1909 running, then in 1912 he rode Worth to victory in what the National Museum of Racing and Hall of Fame describes as probably his most dramatic win.

On November 19, 1909, The New York Times reported that Shilling severely stabbed stable owner R. L. Thomas after the two got into an argument at Sheepshead Bay Race Track.

On November 2, 1911, The New York Times reported that Carroll Shilling and trainer Sam Hildreth had sailed to England aboard the RMS Mauretania with the intent of riding there for the stable of American owner Charles Kohler.

As an assistant to trainer H. Guy Bedwell, Shilling helped condition Sir Barton for his 1919 Triple Crown championship and tutored a young jockey named Earl Sande, who would go on to a Hall of Fame career of his own.

On November 11, 1920, The New York Times reported that Ross had successfully petitioned the Maryland State Racing Commission to lift the ban on Shilling and grant him a temporary jockey's license.

The April 21, 1921 issue of The New York Times quoted from a letter by Belmont to Ross saying "the entries of your stable will not be acceptable to this association if ex-Jockey Carroll Shilling or H. G. Bedwell is in any way connected, directly or indirectly, with the same."

Maryland's governor, Albert Ritchie, got involved as did state senator William I. Norris, who acted as legal counsel for trainer Bedwell.