After these successes Lipkin began the transition to the longer distance C-1 500m in preparation for the 2008 Summer Olympics, where there will be no 200 m races. He didn't appear at the 2006 European Senior Championships; instead he was entered for the under-23 championships in Schinias, Greece, where he won two titles, the C-1 500m and also the C-2 500m (with Ilya Shtokalov). At the senior world championships in Szeged. Hungary. however he returned to the 200 m distance and became individual C-1 champion ahead of Ukraine's Valentin Demyanenko. Lipkin won a silver in the C-4 200 m event at the 2007 championships in Duisburg. He also won five medals at the 2009 championships in Dartmouth (Gold: C-1 4 x 200 m, Silver: C-1 200 m, C-1 500 m, C-4 200 m; Bronze: C-2 1000 m), the most among any Canadian canoeist at the championships. Lipkin added gold again in 2010, but only in the C-1 4 x 200 m.