In 2010, Woodlock accepted the guilty plea of Dianne Wilkerson, a former member of the Massachusetts Senate who pleaded guilty to attempted extortion and admitted that she had accepted bribes, and the next year, Woodlock sentenced her to three and a half years in prison. Also in 2011, Woodlock sentenced former Boston city councilor Chuck Turner to three years in prison for accepting a $1,000 bribe, citing Turner's false statements to the FBI and "ludicrously perjurious testimony" as reasons for the sentence. In 2012, Woodlock sentenced Catherine E. Greig, the longtime companion of Boston organized crime figure James "Whitey" Bulger, to eight years in jail. Greig pleaded guilty to harboring Bulger while he was a fugitive from justice. The sentence was affirmed on appeal. In 2014, Woodlock oversaw the criminal proceedings against two friends of Boston Marathon bomber Dzhokhar Tsarnaev, who were convicted of obstruction of justice for destroying evidence and lying to authorities who were investigating the crime. In 2019, Woodlock was the judge assigned to the criminal case against Jeffrey Bizzack, a California businessman who was one of many parents charged in the Varsity Blues admissions bribery scandal. Bizzack pleaded guilty to conspiracy to commit fraud in connection with a scheme to get his son admitted to the University of Southern California as a fake recruited athlete; Woodlock sentenced Bizzack to two months in prison, three years of supervised release, and a $250,000 fine.