 On June 12, 2013, Douglass signed a two-year deal with Israeli team Hapoel Gilboa Galil.On November 24, 2013, Douglass recorded a season-high 18 points, shooting 8-of-13 from the field, along with six assists and two steals in a 63–73 loss to Barak Netanya.Douglass helped Gilboa Galil reach the 2014 Israeli League Quarterfinals, as well as reaching the 2014 Balkan League Finals, where they eventually lost to Levski Sofia.