Lipsky played college golf at Northwestern University where he was an All-American and won the 2010 Big Ten individual championship.

Since that victory, he has competed predominantly on the European Tour and won for the second time at the Alfred Dunhill Championship in 2018.

[8] Lipsky played college golf at Northwestern University, which he attended on a partial scholarship and at which he majored in political science and history.

In 2007–08, he had a number one finish with a 139 at the Notre Dame Invitational, and won the Jacksonville Dual Match with a 68.

[3] He had a 72.02 stroke average in the regular season, seventh-best in school season history, and ended with a career 72.97 stroke average, the fourth-best in school history behind Luke Donald, Tom Johnson, and Jess Daley.

[15] Lipsky won the Omega European Masters (earning a career-best €383,330 ($497,000)) and finished the Asian Tour season leading the Order of Merit, which also earned him entry into his first major (2015 Open Championship) and first WGC event (2015 WGC-Cadillac Championship) and a European Tour exemption through 2016.

[16] On December 16, 2018, Lipsky won the Alfred Dunhill Championship at Leopard Creek Country Club in South Africa.