Grigor Dimitrov (Bulgaria) 3 - 5 Janko Tipsarevic (Serbia)

Date	Tournament	Surface	Rd	Opp. Rank	Winner	Score
26 May 2019	Roland Garros Paris, France Grand Slam	Clay	R128	317	Grigor Dimitrov (BUL)	6-3 6-0 3-6 6-7(4) 6-4
14 Jan 2019	Australian Open Melbourne, Australia Grand Slam	Hard	R128		Grigor Dimitrov (BUL)	4-6 6-3 6-1 6-4
13 Jun 2016	Fever-Tree Championships London / Queen`s Club, Great Britain ATP Tour 500	Grass	R32	552	Janko Tipsarevic (SRB)	6-7(6) 6-4 3-6
18 Jun 2013	The Boodles Challenge Stoke Park, Great Britain Exhibition	Grass	Q	14	Janko Tipsarevic (SRB)	7-6(5) 6-7(5) [4-10]
16 Apr 2013	Monte-Carlo Rolex Masters Monte-Carlo, Monaco ATP Tour Masters	Clay	R32	10	Grigor Dimitrov (BUL)	7-6(3) 6-1
27 Mar 2012	Miami Open Miami, Florida, USA ATP Tour Masters	Hard	R16	9	Janko Tipsarevic (SRB)	6-7(3) 2-6
04 Aug 2011	Citi Open Washington, DC, USA ATP Tour 500	Hard	R16	25	Janko Tipsarevic (SRB)	4-6 2-6
16 Jun 2011	Aegon International Eastbourne, Great Britain ATP Tour 250	Grass	Q	30	Janko Tipsarevic (SRB)	3-6 6-7(2)