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2026

  • Wed, August 26, 2026

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      Varsity Football - Boys Holy Cross

      4:30PM - 5:30PM EDT

      Plainville High School - Plainville HS- Tinty Stadium
      Scrimmage Away vs Watertown
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      Varsity Football - Boys Holy Cross

      4:30PM - 5:30PM EDT

      Plainville High School - Plainville HS- Tinty Stadium
      Scrimmage Away vs Wethersfield

  • Sat, August 29, 2026

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      Varsity Soccer - Boys Holy Cross

      8:00AM - 9:00AM EDT

      Shelton High School - Finn Stadium
      Scrimmage Away vs East Haven
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      Varsity Soccer - Boys Holy Cross

      8:00AM - 9:00AM EDT

      Shelton High School - Finn Stadium
      Scrimmage Away vs Shelton
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      Varsity Football - Boys Holy Cross

      10:00AM - 11:00AM EDT

      Seymour High School - turf field
      League Away vs Seymour
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      Varsity Soccer - Girls Holy Cross

      2:00PM - 3:00PM EDT

      Thomaston Nystrom Park - Nystrom Park Field
      Non-League Away vs Thomaston

  • Mon, August 31, 2026

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      Varsity Soccer - Girls Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      Scrimmage Home vs Haddam Killingworth
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      Varsity Volleyball - Girls Holy Cross

      4:00PM - 5:00PM EDT

      Mercy High School - Gym
      Scrimmage Away vs Mercy

  • Thu, September 03, 2026

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      Varsity Football - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Bowen Field - Football Field
      Scrimmage Away vs Hillhouse
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      Varsity Volleyball - Girls Holy Cross

      5:00PM - 6:00PM EDT

      Holy Cross - Tim McDonald Gymnasium
      Scrimmage Home vs Lewis Mills

  • Fri, September 04, 2026

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      Varsity Volleyball - Girls Holy Cross

      5:15PM - 6:15PM EDT

      Nonnewaug High School - Gym
      Scrimmage Away vs Nonnewaug

  • Thu, September 10, 2026

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      Varsity Soccer - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs Oxford
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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Holy Cross - Tim McDonald Gymnasium
      League Home vs Wolcott
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      Varsity Football - Boys Holy Cross

      7:00PM - 8:00PM EDT

      Municipal Stadium South Field - Ray Snyder, Sr. Turf Field
      League Home vs Naugatuck

  • Fri, September 11, 2026

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      Froshmore Football - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Naugatuck High School - Veterans Field
      League Away vs Naugatuck
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      Varsity Soccer - Girls Holy Cross

      4:00PM - 5:00PM EDT

      Nolan Field-Ansonia - Soccer Field
      League Away vs Ansonia
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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Holy Cross - Tim McDonald Gymnasium
      League Home vs Derby

  • Sat, September 12, 2026

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      Junior Varsity Soccer - Boys Holy Cross

      10:00AM - 11:00AM EDT

      Watertown High School - John J. Mills Complex @ Watertown High School
      League Away vs Watertown

  • Mon, September 14, 2026

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      Varsity Soccer - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs Wilby

  • Tue, September 15, 2026

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      Varsity Cross Country - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Holy Cross - Holy Cross
      League Home vs Oxford
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      Varsity Cross Country - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Holy Cross - Holy Cross
      League Home vs Torrington
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      Varsity Cross Country - Girls Holy Cross

      3:45PM - 4:45PM EDT

      Holy Cross - Holy Cross
      League Home vs Oxford
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      Varsity Cross Country - Girls Holy Cross

      3:45PM - 4:45PM EDT

      Holy Cross - Holy Cross
      League Home vs Torrington
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      Varsity Soccer - Girls Holy Cross

      4:00PM - 5:00PM EDT

      St. Paul Catholic HS - McPhee Field
      League Away vs St. Paul Catholic
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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Naugatuck High School - Edward Mariano Gymnasium
      League Away vs Naugatuck

  • Wed, September 16, 2026

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      Varsity Soccer - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Municipal Stadium South Field - Ray Snyder, Sr. Turf Field
      League Away vs Kennedy

  • Thu, September 17, 2026

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      Varsity Soccer - Girls Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs Torrington
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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Holy Cross - Tim McDonald Gymnasium
      League Home vs Torrington

  • Fri, September 18, 2026

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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Crosby High School - CHS - Augelli Court
      League Away vs Crosby
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      Varsity Football - Boys Holy Cross

      6:30PM - 7:30PM EDT

      Brookfield High School - BHS Stadium Field
      League Away vs Brookfield

  • Sat, September 19, 2026

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      Junior Varsity Football - Boys Holy Cross

      10:00AM - 11:00AM EDT

      Brookfield High School - BHS Stadium Field
      League Away vs Brookfield

  • Mon, September 21, 2026

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      Varsity Soccer - Boys Holy Cross

      7:00PM - 8:00PM EDT

      Watertown High - John J Mills Complex @ Watertown HS
      League Away vs Watertown

  • Tue, September 22, 2026

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      Varsity Soccer - Girls Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs Woodland
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      Varsity Cross Country - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Wolcott High School - Wolcott High School, Lower Soccer Field
      League Away vs Seymour
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      Varsity Cross Country - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Wolcott High School - Wolcott High School, Lower Soccer Field
      League Away vs Wolcott
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      Varsity Cross Country - Girls Holy Cross

      3:30PM - 4:30PM EDT

      Wolcott High School - WHS Track and Lower Field
      League Away vs Seymour
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      Varsity Cross Country - Girls Holy Cross

      3:30PM - 4:30PM EDT

      Wolcott High School - WHS Track and Lower Field
      League Away vs WCA
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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Holy Cross - Tim McDonald Gymnasium
      Non-League Home vs Brookfield

  • Wed, September 23, 2026

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      Varsity Soccer - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs Wolcott
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      Junior Varsity Soccer - Girls Holy Cross

      3:45PM - 4:45PM EDT

      Woodland High School - Woodland Soccer Field
      League Away vs Woodland

  • Thu, September 24, 2026

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      Varsity Soccer - Girls Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs Watertown
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      Junior Varsity Soccer - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Wolcott High School - Wolcott High School, Lower Soccer Field
      League Away vs Wolcott
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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Holy Cross - Tim McDonald Gymnasium
      League Home vs St. Paul Catholic

  • Fri, September 25, 2026

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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Seymour High School - Gym
      League Away vs Seymour
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      Varsity Football - Boys Holy Cross

      6:30PM - 7:30PM EDT

      Municipal Stadium South Field - Ray Snyder, Sr. Turf Field
      League Home vs Watertown
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      Varsity Soccer - Boys Holy Cross

      6:30PM - 7:30PM EDT

      St. Paul Catholic HS - McPhee Field
      League Away vs St. Paul Catholic

  • Sat, September 26, 2026

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      Junior Varsity Football - Boys Holy Cross

      10:15AM - 11:15AM EDT

      Watertown High - John J Mills Complex @ Watertown HS
      League Away vs Watertown

  • Mon, September 28, 2026

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      Varsity Soccer - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs Woodland
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      Varsity Soccer - Girls Holy Cross

      4:00PM - 5:00PM EDT

      Wolcott High School - Turf Field
      League Away vs Wolcott

  • Tue, September 29, 2026

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      Varsity Volleyball - Girls Holy Cross

      12:01AM - 1:01AM EDT

      Woodland High School - Gym
      League Away vs Woodland
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      Varsity Cross Country - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Woodland High School - Track
      League Away vs Woodland
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      Varsity Cross Country - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Woodland High School - Track
      League Away vs Naugatuck
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      Varsity Cross Country - Girls Holy Cross

      3:45PM - 4:45PM EDT

      Woodland High School - Track
      League Away vs Naugatuck
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      Varsity Cross Country - Girls Holy Cross

      3:45PM - 4:45PM EDT

      Woodland High School - Track
      League Away vs Wilby

  • Wed, September 30, 2026

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      Varsity Soccer - Girls Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs St. Paul Catholic
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      Varsity Soccer - Boys Holy Cross

      6:00PM - 7:00PM EDT

      Torrington High School - Robert Frost Sports Complex
      League Away vs Torrington

  • Thu, October 01, 2026

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      Junior Varsity Soccer - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Torrington High School - Robert Frost Sports Complex
      League Away vs Torrington
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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Holy Cross - Tim McDonald Gymnasium
      League Home vs WCA

  • Fri, October 02, 2026

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      Varsity Cross Country - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Nonnewaug High School - XC Course
      Non-League Away
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      Varsity Cross Country - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Nonnewaug High School - XC Course
      Non-League Away vs Shepaug Valley
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      Varsity Cross Country - Girls Holy Cross

      3:45PM - 4:45PM EDT

      Nonnewaug High School - XC Course
      Non-League Away vs Lewis Mills
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      Varsity Cross Country - Girls Holy Cross

      3:45PM - 4:45PM EDT

      Nonnewaug High School - XC Course
      Non-League Away vs Naugatuck
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      Varsity Football - Boys Holy Cross

      6:00PM - 7:00PM EDT

      Oxford High School - OHS Wolverine Field (Turf)
      League Away vs Oxford
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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Watertown High - Robert B Cook Memorial Gym
      League Away vs Watertown

  • Sat, October 03, 2026

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      Varsity Volleyball - Girls Holy Cross

      12:01AM - 1:01AM EDT

      Connecticut Sports Center - Connecticut Sports Center
      Non-League Away vs Amity
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      Varsity Volleyball - Girls Holy Cross

      12:01AM - 1:01AM EDT

      Connecticut Sports Center - Connecticut Sports Center
      Non-League Away vs Pomperaug
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      Junior Varsity Soccer - Boys Holy Cross

      10:00AM - 11:00AM EDT

      Woodland High School - Woodland - Turf Field
      League Away vs Woodland

  • Mon, October 05, 2026

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      Varsity Soccer - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs WCA
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      Varsity Soccer - Girls Holy Cross

      3:45PM - 4:45PM EDT

      Naugatuck High School - Veterans Field
      League Away vs Naugatuck

  • Tue, October 06, 2026

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      Varsity Cross Country - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Holy Cross - Holy Cross
      League Home vs Kennedy
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      Varsity Cross Country - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Holy Cross - Holy Cross
      League Home vs Crosby
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      Varsity Cross Country - Girls Holy Cross

      3:45PM - 4:45PM EDT

      Holy Cross - Holy Cross
      League Home vs Derby EOB
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      Varsity Cross Country - Girls Holy Cross

      3:45PM - 4:45PM EDT

      Holy Cross - Holy Cross
      League Home vs Crosby
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      Varsity Volleyball - Girls Holy Cross

      5:15PM - 6:15PM EDT

      Oxford High School - Main Gym
      League Away vs Oxford

  • Wed, October 07, 2026

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      Varsity Soccer - Girls Holy Cross

      12:01AM - 1:01AM EDT

      Woodland High School - Woodland - Turf Field
      League Away vs Woodland
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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Ansonia High School - Gym
      League Away vs Ansonia

  • Thu, October 08, 2026

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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Holy Cross - Tim McDonald Gymnasium
      League Home vs Naugatuck

  • Fri, October 09, 2026

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      Varsity Soccer - Boys Holy Cross

      6:00PM - 7:00PM EDT

      Ansonia High School - Nolan Field
      League Away vs Ansonia
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      Varsity Football - Boys Holy Cross

      6:30PM - 7:30PM EDT

      Municipal Stadium South Field - Ray Snyder, Sr. Turf Field
      League Home vs Ansonia

  • Sat, October 10, 2026

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      Varsity Soccer - Girls Holy Cross

      12:00PM - 1:00PM EDT

      Coginchaug Regional High School - CRHS Stadium Field & Track
      Non-League Away vs Coginchaug

  • Tue, October 13, 2026

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      Varsity Soccer - Girls Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs Oxford
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      Varsity Cross Country - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Watertown High School - Veteran's Park
      League Away vs St. Paul Catholic
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      Varsity Cross Country - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Watertown High School - Veteran's Park
      League Away vs Watertown
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      Varsity Cross Country - Girls Holy Cross

      3:45PM - 4:45PM EDT

      Watertown High School - Veteran's Park
      League Away vs St. Paul Catholic
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      Varsity Cross Country - Girls Holy Cross

      3:45PM - 4:45PM EDT

      Watertown High School - Veteran's Park
      League Away vs Watertown

  • Wed, October 14, 2026

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      Varsity Soccer - Boys Holy Cross

      6:00PM - 7:00PM EDT

      Seymour High School - turf field
      League Away vs Seymour

  • Thu, October 15, 2026

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      Varsity Soccer - Girls Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs Ansonia
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      Junior Varsity Soccer - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Seymour High School - Seymour High Lower Field
      League Away vs Seymour
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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Holy Cross - Tim McDonald Gymnasium
      League Home vs Kennedy

  • Fri, October 16, 2026

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      Varsity Soccer - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs Crosby

  • Mon, October 19, 2026

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      Varsity Soccer - Girls Holy Cross

      6:30PM - 7:30PM EDT

      Watertown High - John J Mills Complex @ Watertown HS
      League Away vs Watertown

  • Tue, October 20, 2026

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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Holy Cross - Tim McDonald Gymnasium
      League Home vs Seymour

  • Wed, October 21, 2026

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      Varsity Cross Country - Girls Holy Cross

      3:30PM - 4:30PM EDT

      Veterans Memorial Park - Veterans Park XC Course
      Postseason Away vs Derby EOB
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      Varsity Cross Country - Girls Holy Cross

      3:30PM - 4:30PM EDT

      Veterans Memorial Park - Veterans Park XC Course
      Postseason Away vs Woodland
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      Varsity Cross Country - Boys Holy Cross

      4:00PM - 5:00PM EDT

      Veterans Memorial Park - Veterans Park XC Course
      Postseason Away vs Crosby
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      Varsity Cross Country - Boys Holy Cross

      4:00PM - 5:00PM EDT

      Veterans Memorial Park - Veterans Park XC Course
      Postseason Away vs Woodland
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      Varsity Soccer - Boys Holy Cross

      6:00PM - 7:00PM EDT

      Naugatuck High School - Veterans Field
      League Away vs Naugatuck

  • Thu, October 22, 2026

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      Junior Varsity Soccer - Boys Holy Cross

      3:45PM - 4:45PM EDT

      Rotary Field - Soccer Field
      League Away vs Naugatuck
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      Varsity Soccer - Girls Holy Cross

      4:30PM - 5:30PM EDT

      Municipal Stadium South Field - Ray Snyder, Sr. Turf Field
      League Home vs Seymour
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      Varsity Volleyball - Girls Holy Cross

      5:15PM - 6:15PM EDT

      Wilby High School - George Tirado Floor @ The Reggie O'Brien Gymnasium
      League Away vs Wilby
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      Varsity Soccer - Boys Holy Cross

      7:00PM - 8:00PM EDT

      Municipal Stadium South Field - Ray Snyder, Sr. Turf Field
      League Home vs Naugatuck

  • Fri, October 23, 2026

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      Varsity Soccer - Boys Holy Cross

      3:30PM - 4:30PM EDT

      Holy Cross - Alumni Field
      League Home vs Derby

  • Sat, October 24, 2026

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      Varsity Football - Boys Holy Cross

      10:00AM - 11:00AM EDT

      Crosby High School - CHS - Jimmy Lee Stadium (Turf)
      League Away vs Crosby
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      Varsity Soccer - Boys Holy Cross

      11:00AM - 12:00PM EDT

      Holy Cross - Alumni Field
      Non-League Home vs Brookfield
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      Varsity Soccer - Girls Holy Cross

      12:00PM - 1:00PM EDT

      Brookfield High School - BHS Stadium Field
      League Away vs Brookfield

  • Mon, October 26, 2026

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      Varsity Soccer - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Leo F. Ryan Athletic Complex - DeFilippo Field
      League Away vs Derby EOB

  • Tue, October 27, 2026

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      Varsity Volleyball - Girls Holy Cross

      6:00PM - 7:00PM EDT

      Holy Cross - Tim McDonald Gymnasium
      League Home vs Woodland

  • Thu, October 29, 2026

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      Varsity Volleyball - Girls Holy Cross

      5:15PM - 6:15PM EDT

      Waterbury Career Academy - Gymnasium
      League Away vs WCA
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      Varsity Football - Boys Holy Cross

      6:30PM - 7:30PM EDT

      Municipal Stadium South Field - Ray Snyder, Sr. Turf Field
      League Home vs WCA

  • Fri, November 06, 2026

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      Varsity Football - Boys Holy Cross

      6:30PM - 7:30PM EDT

      Woodland High School - Woodland - Turf Field
      League Away vs Woodland

  • Thu, November 12, 2026

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      Varsity Football - Boys Holy Cross

      6:30PM - 7:30PM EDT

      Municipal Stadium South Field - Ray Snyder, Sr. Turf Field
      League Home vs GNH
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