|Team Name||Under Achievers|
|Best Season||8-5 (2010)|
|Worst Season||2-11 (2013)|
|Conference Titles||1 (2016)|
|KSL Championship||1 (2016)|
2007-2009 - Playoff Drought
Jon had joined KSL in 2007 but suffered the dreaded first year failures. He went 4-9 his first year in the league and failed to make the playoffs. Instead he battled for a high draft pick for the following year.
In 2008 Jon was placed in a tough division alongside the top scoring Andrew Hughes and Kevin Smith. Oberg suffered many defeats that year going 3-9 overall. He failed to make the playoffs and was subsequently placed into the lottery for draft position.
2009 saw Jon go 3-9 again. This year he was placed in the other conference to fill the hole left by Andy McConnell. Jon had stiff competition from his divisional opponents Snider and Doug. Oberg had failed to make it into the playoffs by a couple games but earned a high draft spot for the following year.
Jon's first 3 season records netted him a 10-27 Record but his next 2 gave him a 16-10 record.
2010, 2011 - Rising to the Top
Jon was sick of failure and decided to turn his team around. He did mock drafts and studied the waiver wires to achieve a better overall record and make it into the playoffs.
Jon started the 2010 season going 7-2 before going on a 3 game losing streak. Jon achieved his dream of having a winning record of 8-5 and making it into the playoffs. He had lost 2 straight matches but he beat rival Aaron Hughes to place 7th in the playoffs.
In 2011 Jon had drafted a great team but had lousy luck. His division was the highest scoring in the league and had the best overall record. This caused some problems with Jon being able to make his way into the top tier teams. Jon started off going 1-5 but was able to 5-1 in his next 6 games including a win over the top scoring Joe Snider. Even with all these difficulties, Jon was able to make it into the playoffs. Once again, he lost the first round by only a few points to Dave Pate. He was able to finish 7th overall beating the 2nd seeded team Dave Nanninga.
2012 - 2017
Oberg started off the 2012 season strong by defeating divisional rival Joe Snider. However, Jon would lose his next 3 games to teams that would finish above 500. Jon was able to get back at his winning ways by securing another divisional win against Doug and start out 2-3. However, Jon would lose his next 4 games and be placed at the bottom of KSL. He was able to secure 2 more wins towards the end of the season but he still finished 12th overall. This was a major disappointment for Jon since he hadn't finished last during his KSL career.
In 2013 Jon Oberg started off hot by defeating long time rival Aaron Hughes in the first matchup of the season. However, this would be only one of two games he would win all year. Week after week Jon lost games by a few points and eventually lost 10 straight before finally defeating Dave Nanninga. This win over Dave knocked him out of the playoffs.
For 2014 Jon has a couple extra early round picks and is hoping to turn them into superstars. Early on, it wasn't very fruitful as he lost his first 2 games. Jon was able to turn it around and take 3 of his next 4 to break even half way through the season. Jon ended up losing 3 in a row and it looked like he may not make it into the playoffs. Jon was able to take those early mistakes and win his next 4 regular season games to finish the year 7-6. Jon was able to take down Ty Palmer in round 1 of the playoffs but was unable to defeat the red hot Dave Nanninga in the second round. Jon's journey back to the playoffs made him a happy man. Despite losing in the second round, Jon went on to finish 3rd.
2015 saw Jon stay in a similar division but added Dave Pate and move Aaron to a new division. Jon started the season with a couple of losses but bounced back with winning 3 of his next 4. Jon was 3-3 but he had a rough second half of the season. Jon got a key win over Brian and Ty Palmer but was unable to win any other divisional game and finished the season at 5-8. Jon missed the playoffs this year but was looking to 2016 to bounce back and make it back to the playoffs.
2016 was a strange season for Jon. He was 4-4 at one point and second in his division but he lost 4 straight games and was put into a win and in situation for Week 13. There was 1 spot open and the winner of Dave Pate and Jon Oberg would make it in. Jon was lucky enough to get a win but had an uphill battle against the 11-2 Ty Palmer. Luckily for Jon, Ty's team fell apart and he was able to move on to divisional winner and #2 seed Kevin Smith. Again, Jon was able to beat the competition and go on to the finals for the first time in his career. He was taking on Andy in what would be a first ever championship match for the two. Jon was able to defeat Andy by a slim margin and take home the crown of the 2016 KSL Championship.
2017 was similar to 2013 for Jon. He got a win early in the season but had a string of loses in the middle which killed his playoff chances. Jon finished 2017 at 2-11. It was unfortunate for Jon after having won KSL but he was ready for 2018 to come.