| Us | Them | Record | Box Score |
| BEARS 51 | Wilde Lake 21 | 1-0 | click |
| BEARS 23 | Calvert Hall 30 | 1-1 | click |
| BEARS 48 | St. Paul’s 16 | 2-1 | click |
| BEARS 63 | Glenelg 4 | 3-1 | click |
| BEARS 22 | South Carroll 47 | 3-2 | click |
| BEARS 48 | Mt. Hebron 12 | 4-2 | click |
| BEARS 21 | Old Mill 37 | 4-3 | click |
| BEARS 54 | Long Reach 13 | 5-3 | click |
| BEARS 63 | Howard 12 | 6-3 | click |
| BEARS 61 | Centennial 6 | 7-3 | click |
| BEARS 51 | Oakland Mills 17 | 8-3 | click |
| BEARS 24 | Atholton 26 | 8-4 | click |
| BEARS 18 | River Hill 36 | 8-5 | click |
| BEARS 36 | Poolesville 30 (Regional Semi-Finals) |
9-5 | click |
| BEARS 26 | Atholton 23 (Regional Finals) |
10-5 | click |
| BEARS 24 | Kent 31 (State Semi-Finals) |
10-6 | click |
2000 TOURNAMENT RESULTS
Western Branch Rotational – (12/10-11/1999)
10th Place – (1-8) View Full Results
- Ryan Mackin – 2nd
- Jason Freiert – 4th
- Will Shields – 6th
- Kevin Chrapaty – 6th
Lackey Christmas Invitational – (12/17-18/1999)
5th Place – 123 Points View Full Results
- Jason Freiert – 3rd
- Jimmy Davis – 3rd
- Rob Osborn – 3rd
- Ryan Mackin – 3rd
- Joey Killo – 5th
- Russell Tebeleff – 6th
- Scott Wallace – 6th
- Kenton Dunson – 6th
St. Paul’s JV Tournament – (1/8/2000)
- Andy Keats – 1st
- Chad Graham – 1st
- Tim Carter – 1st
- Jon Craig – 1st
- Jarrell Graham – 2nd
- Julius Chang – 2nd
- Adam Gross – 3rd
- Marshall Porter – 3rd
- Manuel Patino – 3rd
- Elliot Cohen – 4th
Hammond Invitational – (1/14-15/2000)
13th Place – 99 Points View Full Results
- Ryan Mackin – 3rd
- Joe Killo – 5th
- Kevin Chrapaty – 6th
Howard County Tournament (Varsity) – (2/19/2000)
2nd Place – 237.5 points
- Jason Freiert – 1st
- Ryan Mackin – 1st
- Joe Killo – 1st
- Rob Osborn – 1st
- Kevin Chrapaty – 1st
- Matt Myers – 3rd
- Jimmy Davis – 3rd
- Dominic Sessa – 3rd
- Scott Wallace – 3rd
- Will Shields – 4th
- Dan Hill – 5th
- Russell Tebeleff – 6th
Howard County Tournament (JV) – (2/19/2000)
1st Place
- Andy Keats – 1st
- Chad Graham – 1st
- Jarrell Graham – 1st
- Marshall Porter – 1st
- Tim Carter – 1st
- Jon Craig – 1st
- Lee Seidman – 2nd
- Mike Azoulay – 3rd
- Brad Palmer – 3rd
1A/2A South Region Tournament – (2/25-26/2000)
2nd Place
- Ryan Mackin – 1st
- Joe Killo – 1st
- Jason Freiert – 2nd
- Jimmy Davis – 2nd
- Rob Osborn – 2nd
- Will Shields – 3rd
- Dominic Sessa – 3rd
- Scott Wallace – 3rd
- Matt Myers – 5th
1A/2A State Tournament – (3/3-4/2000)
10th Place – 45 points
8 State Qualifiers
- Jason Freiert – 4th
- Scott Wallace – 4th
- Rob Osborn – 6th