| 02 Jun 21 | r00        | Chicago SkyChicago Sky | 83 - 84 | Phoenix MercuryPhoenix Mercu |
| 04 Jun 21 | r00        | Phoenix MercuryPhoenix Mercu | 77 - 74 | Chicago SkyChicago Sky |
| 05 Jun 21 | r00        | Los Angeles SparksLos Angeles S | 68 - 63 | Chicago SkyChicago Sky |
| 10 Jun 21 | r00        | Chicago SkyChicago Sky | 92 - 76 | Indiana FeverIndiana Fever |
| 12 Jun 21 | r00        | Indiana FeverIndiana Fever | 79 - 83 | Chicago SkyChicago Sky |
| 16 Jun 21 | r00        | Minnesota LynxMinnesota Lyn | 89 - 105 | Chicago SkyChicago Sky |
| 18 Jun 21 | r00        | Chicago SkyChicago Sky | 81 - 75 | Connecticut SunConnecticut S |
| 19 Jun 21 | r00        | Chicago SkyChicago Sky | 91 - 81 | Connecticut SunConnecticut S |
| 22 Jun 21 | r00        | New York LibertyNew York Libe | 72 - 92 | Chicago SkyChicago Sky |
| 24 Jun 21 | r00        | New York LibertyNew York Libe | 68 - 91 | Chicago SkyChicago Sky |
| 27 Jun 21 | r00        | Connecticut SunConnecticut S | 74 - 58 | Chicago SkyChicago Sky |
| 01 Jul 21 | r00        | Dallas WingsDallas Wings | 81 - 91 | Chicago SkyChicago Sky |
| 03 Jul 21 | r00        | Dallas WingsDallas Wings | 100 - 91 | Chicago SkyChicago Sky |
| 11 Jul 21 | r00        | Chicago SkyChicago Sky | 85 - 89 | Washington MysticsWashington My |
| 15 Aug 21 | r00        | Chicago SkyChicago Sky | 87 - 85 | Seattle StormSeattle Storm |
| 18 Aug 21 | r00        | Chicago SkyChicago Sky | 76 - 80 | Dallas WingsDallas Wings |
| 22 Aug 21 | r00        | Chicago SkyChicago Sky | 95 - 101 | Minnesota LynxMinnesota Lyn |
| 24 Aug 21 | r00        | Atlanta DreamAtlanta Dream | 79 - 86 | Chicago SkyChicago Sky |
| 28 Aug 21 | r00        | Seattle StormSeattle Storm | 69 - 73 | Chicago SkyChicago Sky |
| 29 Aug 21 | r00        | Seattle StormSeattle Storm | 75 - 107 | Chicago SkyChicago Sky |
| 01 Sep 21 | r00        | Phoenix MercuryPhoenix Mercu | 103 - 83 | Chicago SkyChicago Sky |
| 03 Sep 21 | r00        | Las Vegas AcesLas Vegas Ace | 90 - 83 | Chicago SkyChicago Sky |
| 05 Sep 21 | r00        | Chicago SkyChicago Sky | 92 - 84 | Las Vegas AcesLas Vegas Ace |
| 12 Sep 21 | r00        | Chicago SkyChicago Sky | 71 - 79 | Washington MysticsWashington My |
| 18 Sep 21 | r00        | Chicago SkyChicago Sky | 70 - 103 | Las Vegas AcesLas Vegas Ace |
| 19 Sep 21 | r00        | Chicago SkyChicago Sky | 98 - 87 | Indiana FeverIndiana Fever |
| |
| 26 Sep 21 | Playoff        | Minnesota LynxMinnesota Lyn | 76 - 89 | Chicago SkyChicago Sky |
| 29 Sep 21 | Playoff        | Connecticut SunConnecticut S | 95 - 101 | Chicago SkyChicago Sky |
| 01 Oct 21 | Playoff        | Connecticut SunConnecticut S | 79 - 68 | Chicago SkyChicago Sky |
| 03 Oct 21 | Playoff        | Chicago SkyChicago Sky | 86 - 83 | Connecticut SunConnecticut S |
| 06 Oct 21 | Playoff        | Chicago SkyChicago Sky | 79 - 69 | Connecticut SunConnecticut S |
| 10 Oct 21 | Playoff        | Phoenix MercuryPhoenix Mercu | 77 - 91 | Chicago SkyChicago Sky |
| 14 Oct 21 | Playoff        | Phoenix MercuryPhoenix Mercu | 91 - 86 | Chicago SkyChicago Sky |
| 16 Oct 21 | Playoff        | Chicago SkyChicago Sky | 86 - 50 | Phoenix MercuryPhoenix Mercu |
| 17 Oct 21 | Playoff        | Chicago SkyChicago Sky | 80 - 74 | Phoenix MercuryPhoenix Mercu |