Stan Wawrinka defeated Andy Murray 6-1 6-2 in the Monte Carlo Masters round of 16 on clay. The upset overturned the form book — Andy Murray came in leading the head-to-head 12–7, defending last year's quarter-final. Stan Wawrinka narrowed the head-to-head to 12–8.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2024-05-27 | Roland Garros | R128 | clay | Stan Wawrinka | 6-4 6-4 6-2 |
| 2022-08-15 | Cincinnati Masters | R64 | hard | Andy Murray | 7-6(3) 5-7 7-5 |
| 2020-09-28 | Roland Garros | R128 | clay | Stan Wawrinka | 6-1 6-3 6-2 |
| 2019-10-14 | Antwerp | F | hard | Andy Murray | 3-6 6-4 6-4 |
| 2018-06-25 | Eastbourne | R32 | grass | Andy Murray | 6-1 6-3 |
| 2017-05-29 | Roland Garros | SF | clay | Stan Wawrinka | 6-7(6) 6-3 5-7 7-6(3) 6-1 |
| 2016-11-14 | Tour Finals | RR | hard | Andy Murray | 6-4 6-2 |
| 2016-05-23 | Roland Garros | SF | clay | Andy Murray | 6-4 6-2 4-6 6-2 |
| 2015-11-15 | Tour Finals | RR | hard | Stan Wawrinka | 7-6(4) 6-4 |
| 2013-08-26 | US Open | QF | hard | Stan Wawrinka | 6-4 6-3 6-2 |
| 2012-10-01 | Tokyo | QF | hard | Andy Murray | 6-2 3-6 6-2 |
| 2012-07-25 | London Olympics | R64 | grass | Andy Murray | 6-3 6-3 |
| 2011-10-09 | Shanghai Masters | R16 | hard | Andy Murray | 6-4 3-6 6-3 |
| 2010-08-30 | US Open | R32 | hard | Stan Wawrinka | 6-7(3) 7-6(4) 6-3 6-3 |
| 2009-06-22 | Wimbledon | R16 | grass | Andy Murray | 2-6 6-3 6-3 5-7 6-3 |
| 2008-08-25 | US Open | R16 | hard | Andy Murray | 6-1 6-3 6-3 |
| 2008-07-21 | Canada Masters | R16 | hard | Andy Murray | 6-2 0-6 6-4 |
| 2008-05-05 | Rome Masters | R32 | clay | Stan Wawrinka | 6-2 7-6(5) |
| 2008-02-11 | Marseille | R16 | hard | Andy Murray | 3-6 7-6(5) 6-1 |
Averages from each player's recent completed matches (19 vs 20). ATP, WTA & Challenger.