| Windy City B. Games/Schedule |
| Regular Season |
| Nov. 2, 2018 | Day 1 | Lakeland M. - Windy City B. | 71-96  |
| Nov. 3, 2018 | Day 2 | Windy City B. - Grand Rapids D. | 108-125  |
| Nov. 7, 2018 | Day 6 | Grand Rapids D. - Windy City B. | 114-105 |
| Nov. 9, 2018 | Day 8 | Windy City B. - Capital City Go-Go | 108-117 |
| Nov. 11, 2018 | Day 10 | Raptors 905 - Windy City B. | 111-91 |
| Nov. 14, 2018 | Day 13 | Windy City B. - Memphis H. | 92-110 |
| Nov. 16, 2018 | Day 15 | Windy City B. - Grand Rapids D. | 96-93 |
| Nov. 17, 2018 | Day 16 | Windy City B. - Wisconsin H. | 101-98 |
| Nov. 21, 2018 | Day 20 | Windy City B. - Raptors 905 | 99-91 |
| Nov. 23, 2018 | Day 21 | Long Island N. - Windy City B. | 113-99 |
| Nov. 25, 2018 | Day 23 | Ft.Wayne MA - Windy City B. | 105-100 |
| Nov. 27, 2018 | Day 25 | Windy City B. - Westchester K. | 72-91 |
| Nov. 29, 2018 | Day 27 | Windy City B. - Maine RC | 106-105 |
| Dec. 1, 2018 | Day 29 | Windy City B. - Ft.Wayne MA | 77-98 |
| Dec. 3, 2018 | Day 31 | South Bay L. - Windy City B. | 107-101 |
| Dec. 8, 2018 | Day 36 | Windy City B. - Canton C. | 91-101 |
| Dec. 12, 2018 | Day 40 | Windy City B. - Long Island N. | 89-103 |
| Dec. 14, 2018 | Day 42 | Canton C. - Windy City B. | 96-108 |
| Dec. 15, 2018 | Day 43 | Capital City Go-Go - Windy City B. | 103-111 |
| Dec. 21, 2018 | Day 46 | Windy City B. - Iowa W. | 115-103 |
| Dec. 19, 2018 | Day 46 | NAZ Suns - Windy City B. | 87-99 |
| Dec. 28, 2018 | Day 47 | Windy City B. - OKC Blue | 104-90 |
| Jan. 1, 2019 | Day 51 | Greensboro S. - Windy City B. | 103-117 |
| Jan. 4, 2019 | Day 54 | Windy City B. - Erie Bay H. | 120-118 |
| Jan. 5, 2019 | Day 55 | Stockton K. - Windy City B. | 114-123 |
| Jan. 11, 2019 | Day 61 | Wisconsin H. - Windy City B. | 101-124 |
| Jan. 12, 2019 | Day 62 | Greensboro S. - Windy City B. | 120-96 |
| Jan. 18, 2019 | Day 68 | Erie Bay H. - Windy City B. | 107-103 |
| Jan. 21, 2019 | Day 71 | Westchester K. - Windy City B. | 92-95 |
| Jan. 23, 2019 | Day 73 | Windy City B. - Wisconsin H. | 109-118 |
| Jan. 26, 2019 | Day 76 | Windy City B. - Raptors 905 | 98-102 |
| Jan. 30, 2019 | Day 80 | Windy City B. - Delaware BC | 119-110 |
| Feb. 2, 2019 | Day 82 | Windy City B. - Canton C. | 120-77 |
| Feb. 5, 2019 | Day 85 | Capital City Go-Go - Windy City B. | 109-121 |
| Feb. 8, 2019 | Day 88 | Windy City B. - Ft.Wayne MA | 116-98 |
| Feb. 9, 2019 | Day 89 | Grand Rapids D. - Windy City B. | 113-92 |
| Feb. 12, 2019 | Day 92 | Wisconsin H. - Windy City B. | 110-126 |
| Feb. 20, 2019 | Day 95 | Agua Caliente C. - Windy City B. | 111-107 |
| Feb. 22, 2019 | Day 97 | Ft.Wayne MA - Windy City B. | 112-119 |
| Feb. 24, 2019 | Day 99 | Windy City B. - Maine RC | 113-121 |
| Mar. 1, 2019 | Day 104 | Lakeland M. - Windy City B. | 102-130 |
| Mar. 3, 2019 | Day 106 | Santa Cruz W. - Windy City B. | 105-120 |
| Mar. 7, 2019 | Day 110 | Windy City B. - Westchester K. | 118-127 |
| Mar. 9, 2019 | Day 112 | Windy City B. - Greensboro S. | 113-107 |
| Mar. 13, 2019 | Day 116 | Maine RC - Windy City B. | 127-130 |
| Mar. 15, 2019 | Day 118 | Delaware BC - Windy City B. | 111-121 |
| Mar. 19, 2019 | Day 122 | Windy City B. - Lakeland M. | 109-141 |
| Mar. 22, 2019 | Day 125 | Windy City B. - Erie Bay H. | 101-115 |
| Mar. 23, 2019 | Day 126 | Canton C. - Windy City B. | 120-109 |
| 1/8 Finals |
| Mar. 27, 2019 | Day 127 | Windy City B. - Westchester K. | 82-95 |
| Windy City B. Games/Schedule |
| Nov. 2, 2018 | Round 1 (Regular Season) | Lakeland M. - Windy City B. | 71-96 |
| Nov. 3, 2018 | Round 2 (Regular Season) | Windy City B. - Grand Rapids D. | 108-125 |
| Nov. 7, 2018 | Round 6 (Regular Season) | Grand Rapids D. - Windy City B. | 114-105 |
| Nov. 9, 2018 | Round 8 (Regular Season) | Windy City B. - Capital City Go-Go | 108-117 |
| Nov. 11, 2018 | Round 10 (Regular Season) | Raptors 905 - Windy City B. | 111-91 |
| Nov. 14, 2018 | Round 13 (Regular Season) | Windy City B. - Memphis H. | 92-110 |
| Nov. 16, 2018 | Round 15 (Regular Season) | Windy City B. - Grand Rapids D. | 96-93 |
| Nov. 17, 2018 | Round 16 (Regular Season) | Windy City B. - Wisconsin H. | 101-98 |
| Nov. 21, 2018 | Round 20 (Regular Season) | Windy City B. - Raptors 905 | 99-91 |
| Nov. 23, 2018 | Round 21 (Regular Season) | Long Island N. - Windy City B. | 113-99 |
| Nov. 25, 2018 | Round 23 (Regular Season) | Ft.Wayne MA - Windy City B. | 105-100 |
| Nov. 27, 2018 | Round 25 (Regular Season) | Windy City B. - Westchester K. | 72-91 |
| Nov. 29, 2018 | Round 27 (Regular Season) | Windy City B. - Maine RC | 106-105 |
| Dec. 1, 2018 | Round 29 (Regular Season) | Windy City B. - Ft.Wayne MA | 77-98 |
| Dec. 3, 2018 | Round 31 (Regular Season) | South Bay L. - Windy City B. | 107-101 |
| Dec. 8, 2018 | Round 36 (Regular Season) | Windy City B. - Canton C. | 91-101 |
| Dec. 12, 2018 | Round 40 (Regular Season) | Windy City B. - Long Island N. | 89-103 |
| Dec. 14, 2018 | Round 42 (Regular Season) | Canton C. - Windy City B. | 96-108 |
| Dec. 15, 2018 | Round 43 (Regular Season) | Capital City Go-Go - Windy City B. | 103-111 |
| Dec. 21, 2018 | Round 46 (Regular Season) | Windy City B. - Iowa W. | 115-103 |
| Dec. 19, 2018 | Round 46 (Regular Season) | NAZ Suns - Windy City B. | 87-99 |
| Dec. 28, 2018 | Round 47 (Regular Season) | Windy City B. - OKC Blue | 104-90 |
| Jan. 1, 2019 | Round 51 (Regular Season) | Greensboro S. - Windy City B. | 103-117 |
| Jan. 4, 2019 | Round 54 (Regular Season) | Windy City B. - Erie Bay H. | 120-118 |
| Jan. 5, 2019 | Round 55 (Regular Season) | Stockton K. - Windy City B. | 114-123 |
| Jan. 11, 2019 | Round 61 (Regular Season) | Wisconsin H. - Windy City B. | 101-124 |
| Jan. 12, 2019 | Round 62 (Regular Season) | Greensboro S. - Windy City B. | 120-96 |
| Jan. 18, 2019 | Round 68 (Regular Season) | Erie Bay H. - Windy City B. | 107-103 |
| Jan. 21, 2019 | Round 71 (Regular Season) | Westchester K. - Windy City B. | 92-95 |
| Jan. 23, 2019 | Round 73 (Regular Season) | Windy City B. - Wisconsin H. | 109-118 |
| Jan. 26, 2019 | Round 76 (Regular Season) | Windy City B. - Raptors 905 | 98-102 |
| Jan. 30, 2019 | Round 80 (Regular Season) | Windy City B. - Delaware BC | 119-110 |
| Feb. 2, 2019 | Round 82 (Regular Season) | Windy City B. - Canton C. | 120-77 |
| Feb. 5, 2019 | Round 85 (Regular Season) | Capital City Go-Go - Windy City B. | 109-121 |
| Feb. 8, 2019 | Round 88 (Regular Season) | Windy City B. - Ft.Wayne MA | 116-98 |
| Feb. 9, 2019 | Round 89 (Regular Season) | Grand Rapids D. - Windy City B. | 113-92 |
| Feb. 12, 2019 | Round 92 (Regular Season) | Wisconsin H. - Windy City B. | 110-126 |
| Feb. 20, 2019 | Round 95 (Regular Season) | Agua Caliente C. - Windy City B. | 111-107 |
| Feb. 22, 2019 | Round 97 (Regular Season) | Ft.Wayne MA - Windy City B. | 112-119 |
| Feb. 24, 2019 | Round 99 (Regular Season) | Windy City B. - Maine RC | 113-121 |
| Mar. 1, 2019 | Round 104 (Regular Season) | Lakeland M. - Windy City B. | 102-130 |
| Mar. 3, 2019 | Round 106 (Regular Season) | Santa Cruz W. - Windy City B. | 105-120 |
| Mar. 7, 2019 | Round 110 (Regular Season) | Windy City B. - Westchester K. | 118-127 |
| Mar. 9, 2019 | Round 112 (Regular Season) | Windy City B. - Greensboro S. | 113-107 |
| Mar. 13, 2019 | Round 116 (Regular Season) | Maine RC - Windy City B. | 127-130 |
| Mar. 15, 2019 | Round 118 (Regular Season) | Delaware BC - Windy City B. | 111-121 |
| Mar. 19, 2019 | Round 122 (Regular Season) | Windy City B. - Lakeland M. | 109-141 |
| Mar. 22, 2019 | Round 125 (Regular Season) | Windy City B. - Erie Bay H. | 101-115 |
| Mar. 23, 2019 | Round 126 (Regular Season) | Canton C. - Windy City B. | 120-109 |
| Mar. 27, 2019 | Round 127 (1/8 Finals) | Windy City B. - Westchester K. | 82-95 |
