Sam Warburg at the ITF Circuit event in Israel. Monroe competed in 29 events in 2005, all but one of which were Futures. He lost in the first round of his only main draw Challenger event singles match, to Zack Fleishman at the Cuenca Challenger. Monroe won his first singles title, South Africa F1 in late October, defeating Stephen Mitchell in the final. 2006 Nicholas started the year by winning the ITF Circuit title in Costa Rica. A month later, he won another ITF title, this time in Nigeria. He reached the semifinals of a USTA Pro Circuit event in Little Rock, before reaching back-to-back finals in India. He lost to Karan Rastogi in Delhi and defeated Sunil-Kumar Sipaeya in Dehradun. He reached another ITF Circuit final in the fall in Japan, where he lost to Satoshi Iwabuchi. At the beginning of the year, Nick won consecutive doubles titles on the ITF Circuit with partner Sam Warburg in Mexico and Costa Rica. 2007 Nicholas began the year by attempting to qualify for the 2007 Australian Open. He defeated Jeremy Chardy in his first round singles qualifying match. He reached consecutive ITF Futures events in Japan, where he lost to Gouichi Motomura both times. He won two titles at ITF Futures events in Mexico and won a USTA Pro Circuit event in Rochester, New York, where he defeated Robert Yim in the final. The fall of 2007 saw Monroe reach the semifinals of USTAPro Circuit events in Manchester, Texas, where he lost to eventual champion Michael McClune, and Waikoloa, Hawaii where he lost to Lester Cook. He partnered with Izak van der Merwe to win the USTA Pro Circuit doubles title in Brownsville, Texas. 2012: Challenger circuit doubles success Nicholas won the Challenger in Medellin, Colombia (doubles) with his partner Maciek Sykut. He also won two doubles Challengers in Mexico with German partner, Simon Stadler. 2013–2015: First Three ATP doubles titles Nicholas had his best year as a professional in 2013, finishing the year with a doubles Ranking of World No. 53. In January 2013, Monroe and partner Raven Klaasen made it to the semifinals of the 2013 Aircel Chennai Open, falling to Benoît Paire and Stanislas Wawrinka, after a surprise quarterfinal win over the #1 Seeds Mahesh Bhupathi and Daniel Nestor. He then teamed up successfully with Simon Stadler to play the Copa Claro in Buenos Aires, Argentina. They made