Winters came off the substitutes bench and scored with his first touch in the 2015–16 Scottish Junior Cup final for Pollok against Beith Juniors. He also scored in the penalty shootout which Pollok eventually lost. In August 2016, Winters rejoined East Kilbride for a second spell, this time in a player-coach role and was reunited with his former Rossvale manager, Martin Lauchlan. However, similarly to his first spell with the side, Winters time with the club was brief and he left in November 2016, due to a combination of work commitments and a lack of playing time.