Clinical researchers, historians, educators and field researchers alike still regularly capture data on paper spreadsheets. In the case of health care and education, data will often contain sensitive personal information, further complicating the process of transcribing paper-based archives into digital form. In this work, we describe a tool that utilizes machine learning and crowd intelligence to automatically transcribe images of paper-based spreadsheets into electronic form while protecting sensitive personal information. Our solution consists of four high-level stages: (1) the extraction of cell-level images from the spreadsheet grid, (2) machine recognition of digits within the cells, (3) human transcription of cell contents that the machine was uncertain of and (4) feedback of human transcription results to the machine to improve future classification performance. We test the algorithm on a novel data-set of 135 heterogeneous clinical flow-sheet images collected from the Massachusetts General Hospital (MGH), 2 hand-drawn spreadsheets, one chalk-board drawing, and one printed table. we demonstrate that our algorithm provides a generalized solution for spreadsheet transcription that maintains privacy, is up to 10 times faster and twice as cost effective than existing alternatives. Our work is valuable both as a tool and as a starting point for the development of better algorithms.