The Virgin Islands had seven delegates on the line in its caucuses on Saturday and all went to Clinton. Then, on Sunday, Puerto Rico had 60 delegates up for grabs in its Democratic primary.
The contests essentially serve as a warm-up act for the big prize: Tuesday's slate of contests in California, New Jersey, New Mexico, Montana and South Dakota.
But for Clinton, who is just 60 votes short of reaching the 2,383 delegates she needs to clinch the Democratic nomination, the two weekend contests place her on the precipice.
Clinton currently has 2,323 delegates -- including 1,769 pledged delegates and 547 superdelegates. Sanders has 1,547 delegates total -- 1,501 pledged and 46 super delegates, according to the latest CNN estimates.
The weekend contests come as Clinton and Sanders battle over Democratic superdelegates -- with Sanders arguing that his stronger polling position against Donald Trump should tip the party's scales in his favor.
Puerto Rico governor Alejandro Garcia Padilla threw his support behind Clinton, offering the former secretary of state an endorsement on Wednesday in a Spanish-language statement.
But other superdelegates say they're not yet ready to drop their consideration of Sanders.
New Hampshire state Sen. Martha Fuller Clark said Thursday that she'd support Sanders, who won her home state back in February.
"It has been exhilarating to see so many young people become enthusiastic with Senator Sanders' campaign. Across the nation millions of young people have become engaged for the first time in the political process. That is particularly true here in New Hampshire, especially in my district which includes the University of New Hampshire campus. It is my hope that those young people will feel that, in me, they have an advocate in the leadership of the New Hampshire Democratic Party," she said in a statement.
Sanders has argued that the system is rigged against him, with superdelegates -- the same people he's attempting to court -- playing an outsized role, and closed primaries limited only to Democrats blocking the party from bringing in new and independent voters.
"It is a pretty dumb system. It is a system of anointment when 400 superdelegates come on board a campaign before anybody else indicated they would be running and certainly at a time when nobody has seen how this entire campaign has played out," he said Tuesday in Monterey, California. "It's an unfair system, it's a dumb system, and it's a system we will change."
Clinton, meanwhile, is looking ahead to the general election and turning her attention to attacking Donald Trump -- with her sharpest remarks yet coming in a speech Thursday in San Diego.
"Donald Trump's ideas aren't just different -- they are dangerously incoherent," Clinton said. "They're not even really ideas -- just a series of bizarre rants, personal feuds, and outright lies."
"He's not just unprepared," she said. "He's temperamentally unfit to hold an office that requires knowledge, stability and immense responsibility."