I 2014 optrådte Bomer i fem projekter. De første to film, ''[[Winter's Tale]]'' og ''[[Rumstation 76|Space Station 76]],'' var kommercielle flop. Den første film, en romantisk og overnaturlig fantasy-dramafilm, blev skrevet og instrueret af [[Akiva Goldsman]] og baseret på [[Mark Helprin]]s roman ''Winter's Tale''. <ref>{{Cite web|first=Sheila|last=O'Malley|date=14. februar 2014|url=https://www.rogerebert.com/reviews/winters-tale-2014|website=Chicago Sun-Times|access-date=2. januar 2018|archive-url=https://web.archive.org/web/20140220194416/http://www.rogerebert.com/reviews/winters-tale-2014|title='Winter's Tale' (2014) – Review|archive-date=20. februar 2014}}</ref> Bomer spiller den unge far til [[Colin Farrell]]s karakter. <ref>{{Cite web|first=Mike Jr.|last=Fleming|url=https://deadline.com/2012/09/akiva-goldsmans-winters-tale-sets-matt-bomer-lucy-griffiths-eva-marie-saint-340789/|title=Akiva Goldsman's 'Winter's Tale' Sets Matt Bomer, Lucy Griffiths, Eva Marie Saint|date=21. september 2012|access-date=4. marts 2018|archive-url=https://web.archive.org/web/20140220194416/http://deadline.com/2012/09/akiva-goldsmans-winters-tale-sets-matt-bomer-lucy-griffiths-eva-marie-saint-340789/|website=[[Deadline Hollywood]]|archive-date=20. februar 2014}}</ref> ''Winter's Tale'' modtog negative anmeldelser. <ref>{{Cite web|url=https://www.rottentomatoes.com/m/winters_tale_2014/|title=Winter's Tale (2014)|publisher=Rotten Tomatoes|access-date=4. maj 2014|archive-url=https://web.archive.org/web/20140220194416/http://www.rottentomatoes.com/m/winters_tale_2014/|archive-date=20. februar 2014}}</ref> Hans anden film var i den [[Sort humor|sorte]] rumfiktionskomedie ''[[Rumstation 76|Space Station 76]]'' af [[Jack Plotnick]] sammen med [[Liv Tyler]] og [[Patrick Wilson]]. <ref>{{Kilde nyheder|url=https://www.deadline.com/2014/03/sony-acquires-international-on-space-station-76/|title=Sony Pictures Worldwide Acquisitions Nabs International Rights To Jack Plotnick's'Space Station 76'|last=The Deadline Team|date=7. marts 2014|work=Deadline Hollywood|access-date=8. marts 2014|archive-url=https://web.archive.org/web/20140220194416/http://www.deadline.com/2014/03/sony-acquires-international-on-space-station-76/|archive-date=20. februar 2014}}</ref> James Rocchi fra ''The Wrap'' sagde; "alle skuespillere er kunstige" og beskrev Bomers præstation med ordene: "som en melankolsk ingeniør med en håndprotese, der minder om en Nintendo Power Glove". <ref>{{Kilde nyheder|url=https://www.thewrap.com/space-station-76-review-liv-tyler-matt-bomer-patrick-wilson/|title='Space Station 76' Review: Liv Tyler and Matt Bomer Find Lust in Space in This Parody-Melodrama|last=Rocchi|first=James|date=15. september 2014|access-date=5. marts 2018|archive-url=https://web.archive.org/web/20140220194416/https://www.thewrap.com/space-station-76-review-liv-tyler-matt-bomer-patrick-wilson/|archive-date=20. februar 2014|publisher=[[TheWrap]]}}</ref>
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