It would be an understatement to say that there have been more than a few times that Cov Cath won football games as the underdog. Looking back at state championship games, alone, the only time Cov Cath was widely considered favorite to win in the state finals was in 2017.

I narrowed it down to what I would consider to be the 5 biggest games where Cov Cath played spoiler and upset the other team by winning. Which do you think was the biggest? Or was there one that wasn't among these five?

1969: Cov Cath vs. Highlands - The Colonels' first win over the Bluebirds.
Cov Cath had two previous years of varsity football, and was on their 3rd head coach in 3 seasons. Highlands was the defending AA state champ, and would be the AA state champ the next year, too. Cov Cath stunned Highlands by beating them 35-6 at Holmes High School, then Covington Catholic's home field.

1987: Cov Cath vs. Paducah-Tilghman - The Colonels win their first state championship.
Cov Cath had grand total zero appearances in the state finals. Paducah-Tilghman was ranked the #1 team in the state coming into the state finals. The Blue Tornado had won their first state championship back in 1973 and then repeated only two years prior in 1985, so some of their seniors (including eventual 1987 Mr. Football winner and future NY Jet Kurt Barber) knew what it was to play and win in the state finals. Additional to Barber, Tilghman also had future University of Kentucky wide receiver Kurt Johnson on their offensive unit, but the Cov Cath defense was able to hold them to 6 points in the game and win it 16-6.

1992: Cov Cath vs. Moeller (OH) - The Colonels become the first NKY team to beat Mighty Moe.
Cov Cath headed up to Galbreath Field in Mason and beat a HEAVILY favored Moeller (OH) team 22-17, handing the Crusaders their first-ever loss to a team from northern Kentucky.

1997: Cov Cath vs. Highlands - The Mudbowl. A 2OT upset by the Colonels to win the (then) longest KHSAA playoff game on record.
Highlands won the regular season game 22-24 in Park Hills. The Bluebirds sideline was loaded with D1 talent, including two 1998 Mr. Football finalists - one who would would win the award. Highlands had a D1-studded team with Jared Lorenzen (HHS '99/Kentucky), Derek Smith (HHS '99/Kentucky), Scott Kuhnhein (HHS '98/Ohio State), Randy Stegman (HHS '98/Miami, OH), and Jess Meloche (HHS '99/Kentucky) all on their team, while Cov Cath only had a single player who would receive a D1 football offer on their sideline, Kirt Doolin (CCH '98/Cincinnati). Highlands jumped out to a 28-6 lead in the playoff game in Fort Thomas, and Cov Cath clawed back from the deficit to tie it up at 28 by the end of regulation. Cov Cath won 41-35 in double-overtime.

2024: Cov Cath vs. Boyle County - Revenge is exacted against Boyle County, a Top 20 nationally ranked team, for the 41-0 state finals the year before.
Boyle County was on a 32-game win streak, which ranks as the 12-longest win streak in state history. Earlier in the season they had traveled to Canton, OH and beated Lakewood St. Edward, who was ranked in the top 10 nationally coming into the game. The year prior Boyle County walloped Cov Cath 41-0 in the 4A state finals. Boyle County was unanimously ranked as the overall #1 team in the state in 2024, were ranked #17 nationally by MaxPreps and #13 nationally by USA Today. Cov Cath traveled to Boyle County in the 4A quarterfinals and surprised many by proceeding to stop the Rebels' first drive and jump out to an immediate 7-0 lead. They led 14-6 at the half, then the Rebels tied it up at 14 and 21 in the 3rd quarter, then after the Colonels settled for a field goal early in the 4Q, Boyle County took their first lead of the game up 28-24 with about 10 minutes left in the game. Cov Cath answered with a touchdown and that was it, with the Colonels handing Boyle County their frist home loss in the playoffs in 11 years.

Mud Bowl was pretty balanced teams. Legendary game but not much of an upset.

Doolin played for UC off the top of my head. Woolf, Madden, Fowee, Pfeiffer were all very good players.

27 minutes ago, El Diablo said:

Mud Bowl was pretty balanced teams. Legendary game but not much of an upset.

Doolin played for UC off the top of my head. Woolf, Madden, Fowee, Pfeiffer were all very good players.

Oh man, good call....I totally left out Kirt Doolin as a D1 football player. Haha, must have taken too many thumps to the head from him as a sophomore and junior.

I agree with the teams being relatively balanced though, all tolled. I think I'd have to say the Boyle County win on Friday was the biggest upset in program history based solely on the fact that Boyle County was ranked in the top 20 nationally. Then if you add in the fact that Cov Cath was in control for so much of the game, and I think you've got to go with that win as the biggest upset.

I believe the 87 Tilghman team was ranked as well by USA Today. Maybe in the South Regional rankings.

And most pundits thought that CovCath team would lose to Montgomery County when they played earlier in the playoffs.

 

37 minutes ago, Colonels_Wear_Blue said:

Oh man, good call....I totally left out Kirt Doolin as a D1 football player. Haha, must have taken too many thumps to the head from him as a sophomore and junior.

I agree with the teams being relatively balanced though, all tolled. I think I'd have to say the Boyle County win on Friday was the biggest upset in program history based solely on the fact that Boyle County was ranked in the top 20 nationally. Then if you add in the fact that Cov Cath was in control for so much of the game, and I think you've got to go with that win as the biggest upset.

Was the 97 regular season matchup the game CovCath missed a field goal at the end of the game that would have won it?

2 minutes ago, colonel-fan said:

Was the 97 regular season matchup the game CovCath missed a field goal at the end of the game that would have won it?

Yes, I think Cov Cath kicker was a lineman. 

20 minutes ago, colonel-fan said:

Was the 97 regular season matchup the game CovCath missed a field goal at the end of the game that would have won it?

17 minutes ago, El Diablo said:

Yes, I think Cov Cath kicker was a lineman. 

Yep. Kevin Goetz.

Not sure how much of an upset it would be considered, but the 2001 playoff win vs Highlands was one that shocked me a little.  That CovCath team finished 9-5 and got trounced by 30 in the regular season but won the playoff game by a FG.  Beat a bad Lexington Catholic team the following week before being ousted by eventual state runner up, Rockcastle County.

There is one interesting game with Ashland in 1968 that I will add as Ashland was coming off of a state championship in 1967, compared to Covington Catholic being in their first year when they lost 33-0 to the Tomcats. To add a little context to this Ashland team to lead into 1968, Ashland needed something to happen for them to reach the playoffs and they were expecting the season to end at 10-1 before Highlands losing to Campbell County in an upset opened the door for Ashland to have that opportunity at the state tournament. They would beat Belfry handily, pull a massive upset over Henderson County in which (true story) most of the coaching staff pitched cots at the school to stay there all week to study their opponent, and then would defeat Elizabethtown 19-14 as double-digit underdogs

Fast forward to 1968 to what was the opener for both teams. Covington Catholic would open up at home defeating the defending state champion 12-0. Ashland was still very good that year, finishing the season 7-3-1. To me, that is a real statement in itself, especially with a program being in its second year. Being in state championship contention was not a regular thing, Covington Catholic had not even won a regional or a district championship at the time but did have a solid winning record in their first season.

The reason the 1997 and 2024 upsets stand out is because of (as others mentioned) the level of talent on each teams like the number of Division I players on the 1997 Highlands teams compared to Covington Catholic, who did not have a player who received a Division I offer. By 1997, Covington Catholic I think had four state titles so they were more than an established program by then. The Boyle upset is incredible like the mud bowl because of the boatload of talent Boyle had and the large victory over Covington Catholic the prior season. This was a four-time defending state champion. Their run has been incredible and this is not the only time over the past decade or so that some have said Boyle is the best team in all six classes and some going as far this season as to debate how Boyle County would fare on a national scale - understandable given their success and what was returning. Covington Catholic was talented, but many expected Boyle County to win big like last season in the state finals. However, they were still Covington Catholic. Still the program that had numerous accomplishments, successful players, a program that thrives on these types of games. So to see them pull something like that out, to me, wasn't totally unexpected and many Boyle County fans knew that they were going to be bringing a fight. This year I saw Boyle County on film - like many I was very impressed. But saw ways that, with the right scheme, like with any team there were vulnerabilities. Covington Catholic had a great run blocking scheme for Boyle's defense.

All this being said. I would take the 1987 season. First off, think of the Covington Catholic teams in the late 2010's. From 2017 - 2019 they went 44-1. That little stretch in the late 2010's amounts to 17 more wins than in the entire decade of the 1970's when Covington Catholic really struggled. I say this because even though the 1969 win was nice, the program would fall after that season for a number of years. The program would improve in the early and mid 1980's, but Covington Catholic wasn't quite the established program they are now in 1987. Despite only one loss in week one, they were big underdogs against a defensive-oriented Paducah Tilghman team led by Joe Phill and Mr. Football Kurt Barber who would eventually play in the NFL. The 1987 win over Paducah Tilghman was the year Covington Catholic was on put on the map - their only loss being in game one to Boone County who reached the state finals multiple times between 1987 and 1994. Just two years prior to that Paducah Tilghman won the state title over Belfry so this was not a new stage to them like it was to Covington Catholic. There were still players on that Paducah Tilghman team that had the experience of winning a state championship.

The next season Covington Catholic capitalized on this experience. The state semifinal game against Ashland in 1988 is still often talked about in this area, one of the greatest games played here where Covington Catholic emerged with a 6-0 victory in overtime. Covington Catholic then would have to play AGAIN in overtime the next week to defeat Paducah Tilghman for their second consecutive title. 1987 - 1989 was a tough stretch for Paducah Tilghman with three consecutive state title losses, the OT loss in 1988 and a 7-3 loss in 1989 to Highlands.

10 hours ago, TCR said:

The next season Covington Catholic capitalized on this experience. The state semifinal game against Ashland in 1988 is still often talked about in this area, one of the greatest games played here where Covington Catholic emerged with a 6-0 victory in overtime. Covington Catholic then would have to play AGAIN in overtime the next week to defeat Paducah Tilghman for their second consecutive title.

That 88 semifinal game was an instant classic. We stopped to get gas in Wurtland and the attendant said he wasn’t expecting much of a game since Ashland had upset Russell the week before. Wow, was he wrong! That was my first time seeing a game at Putnam Stadium, a wonderful high school venue. My memory is getting hazy, but I seem to recall Ashland getting 3 chances at a game winning field goal near the end of regulation. I think there was a delay of game called as the ball was snapped on one try, CovCath jumped offside on the next try, and then finally the missed kick. 
The best CovCath playoff game (non-finals) game I’ve seen.

I am between Boyle County recently and the 1987 championship win against Paducah.
 

The run in the state that Boyle was on until losing to the Colonels was big and long. Counting how overwhelmingly that Boyle won last year’s state championship, what they did this season beating St Edward and all else that they accomplished in their run, I feel like this was a very big accomplishment and upset win for the Colonels. 
 

The 1987 state championship win against Paducah was obviously huge with being Covington Catholic’s first, but that was a pretty big one as well. 

@colonel-fan Russell ended up getting red hot a the right time that year, ripping off six in a row including a 29-27 win against Ashland AT Ashland just three weeks prior to when Ashland beat Russell on the road in the playoffs. That was an Ashland team that started 3-5 and I could see why they would fall under the radar even though they had a sophomore class that would be the impetus behind a state title two seasons later. In the Covington Catholic/Boyle County game thread I mentioned how underrated schemes were. I believe that if a team can cause confusion for their opponent, regardless of the difference in talent with a good scheme it can change the dynamic of the game entirely. Ashland put together an unorthodox mix of zone blitzes that caused confusion even with incredible Covington Catholic quarterback Paul Hladon who would go 4-22 in that game for 28 yards  - to be fair, he had some passes that were dropped and was pressured heavily. To combine with that, Ashland had Mike Johnson who at the time was their all-time leading rusher and that helped to keep the Covington Catholic offense on the sideline while Ashland ran some clock.

Both teams had it deep in the other's territory in the fourth quarter. Covington Catholic had a first and goal from the three. Two of the plays were half to one yard gains and then Ashland's defense was able to hold against the fullback, with two stops for no gain. Then on the other end Ashland had the ball on the Covington Catholic 12 with little time remaining. Ashland got called for a false start on a missed kick and Covington Catholic was not happy with the call. Then Covington Catholic would get called for being off sides. So it was tried again. Some on the Ashland base say that on the third attempt Covington Catholic jumped again but it was not called. 

Then in OT Ashland got to the two where the Covington Catholic defense held and then Covington Catholic would score, and win on a draw play.

I was in diapers at the time of this game and always have wanted to see footage of it as to this day it's talked about quite a lot in the area. Most of what I know about this game I can recall from reading in various articles over the years, especially the ones written by sports reporter Mark Maynard and hearing from people who either played or coached. 

Don't underestimate the 1992 road win over Cincinnati Moeller!

That shocked the entire region for many reasons. Moeller - led that year by Carlos Collins & Bobby Brannen - completely overlooked CovCath and struggled mightily the whole game as they weren't prepared for CovCath at all. Recency bias and the fact it wasn't a postseason game cause many to overlook this now in ways they didn't in the past. 

 

8 minutes ago, BrosefStalin said:

Don't underestimate the 1992 road win over Cincinnati Moeller!

That shocked the entire region for many reasons. Moeller - led that year by Carlos Collins & Bobby Brannen - completely overlooked CovCath and struggled mightily the whole game as they weren't prepared for CovCath at all. Recency bias and the fact it wasn't a postseason game cause many to overlook this now in ways they didn't in the past. 

I was at the game, it was a huge upset, but I think the win over Boyle last week was the biggest upset in CovCath program history. 

I say its got to be the Boyle game followed by the 1992 Moeller game. Just the fact that Boyle went up to St Edwards and laid the smack down on the 3 time defending big school champion in Ohio is very impressive. St Edwards is yet again in the semi-finals so could be 4 time champ but rooting for Moeller. Ohio football is so much bigger and better than KY football. Plus no one gave CCH a chance against Boyle including myself. Someone mentioned Calpreps and Massey both had 42-14 predictions for Boyle over CCH. My prediction was probably even worse for my Colonels. I won't lie, I'm still in shock that we won that game but it was fun to watch. 

Kind of surprised the LaSalle win of 2019 wasn't in the discussion. I just assume the fact that CCH had a superior team coming into that game with a 36-1 record over the previous 2.5 years, so probably not much of a upset hence not making the list or discussion. But LaSalle including that 2019 year won state 4 out of 6 state championships in Ohio Division II. That year La Salle beat Moeller, St, Xavier, and Elder. At the time that was a huge win for the program but nothing compared to the Boyle.